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Preparation of 2-(3-Bromo-1-methylpropyl)-1,3-dioxolan and the Corresponding Chloride from 2-Methylbutyrolactone

Lithium aluminium hydride reduction of ethyl 4-chloro-2-methylbutanoate (4a), derived from 3-methyldihydrofuran-2(3H)-one (2-methylbutyrolactone) (1), gave 4-chloro-2-methylbutan-1-ol (5a), oxidation of which with pyridinium chlorochromate afforded 4-chloro-2-methylbutanal (8a).The aldehyde (8a) was converted into 2-(3′-chloro-1′-methylpropyl)-1,3-dioxolan (7a) in 47percent overall yield from (1). 2-(3′-Bromo-1′-methylpropyl)-1,3-dioxolan (7b) was similarly obtained in 49percent overall yield from (1).Attempted conversion of 3-methyltetrahydrofuran-2-ol (2) into the corresponding cyclic ethylene acetal gave epimeric mixtures of 2-(3′-methyltetrahydrofuran-2′-yloxy)ethanol (6) and 2,2′-ethylenedioxybis(3-methyltetrahydrofuran) (9).

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A synthesis method of famciclovir impurity C (by machine translation)

The invention discloses a famciclovir impurity C synthetic method. Although the current literature reported famciclovir impurity C of structure and associated liquid phase chromatographic behavior, but did not disclose the method for obtaining the impurity. The invention adopts the following technical solutions: (¡À) – alpha – to methyl – gamma – butyrolactone as raw materials, in the open loop in the acetic acid solution hydrobromide (¡À) obtained – 2 – methyl – 4 – bromo butyric acid, then converted into (¡À) – 2 – methyl – 4 – bromo methyl butyrate, then tetrahydro reduction is alcohol, and acetylation by (¡À) – 2 – methyl – 4 – bromo butyl acetate, then directly with 2 – amino – 6 – chloropurine coupling, to obtain 4 – (2 – amino – 6 – chloro – 9 H – 9 – purinyl) – 2 – methyl butyl acetate, finally subjected to the hydrogenation dechlorination to obtain famciclovir impurity C. The directed synthesis of the present invention each step in the reaction is stable and reliable, total reaction yield is relatively high. (by machine translation)

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Tetrahydrofuran – Wikipedia,
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A new one-pot synthetic method for selenium-containing medium-sized alpha,beta-unsaturated cyclic ketones

The reaction of tetrahydroselenopyran-2-one (7) with ethynyllithiums 20a-h, followed by treatment with aqueous 5% H2SO4 successfully led to a two-carbon ring expansion to give the 2-substituted 5,6,7,8-tetrahydroselenocin-4-ones 21a-h in 43-95% yields. Seven- to nine-membered gamma-selena-alpha,beta-unsaturated cyclic ketones 22-26 and a 5,6,7,8-tetrahydrotellurocin-4-one 27 were also prepared from the corresponding selenolactones or tellurolactone in a one-pot reaction.

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A comprehensive characterisation of volatile and fatty acid profiles of legume seeds

Legumes are rich in unsaturated fatty acids, which make them susceptible to (non) enzymatic oxidations leading to undesirable odour formation. This study aimed to characterise the volatile and fatty acid profiles of eleven types of legumes using headspace solid-phase microextraction gas chromatography?mass spectrometry (HS-SPME-GC-MS) and GC coupled with a flame ionisation detector (GC-FID), respectively. Volatile aldehydes, alcohols, ketones, esters, terpenes and hydrocarbons were the chemical groups identified across all the legumes. The lipids comprised palmitic, stearic, oleic, linoleic and alpha-linolenic acids, with unsaturated fatty acids comprising at least 66.1% to 85.3% of the total lipids for the legumes studied. Multivariate data analysis was used to compare volatile and fatty acid profiles between legumes, which allow discriminant compounds pertinent to specific legumes to be identified. Results showed that soybean, chickpea and lentil had distinct volatile and fatty acid profiles, with discriminating volatiles including lactone, ester and ketone, respectively. While all three Phaseolus cultivars shared similar volatile profiles, 3-methyl-1-butanol was found to be the only volatile differentiating them against the other eight legumes. Overall, this is the first time a multivariate data analysis has been used to characterise the volatile and fatty acid profiles across different legume seeds, while also identifying discriminating compounds specific for certain legume species. Such information can contribute to the creation of legume-based ingredients with specific volatile characteristics while reducing undesirable odours, or potentially inform relevant breeding programs.

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Tetrahydrofuran – Wikipedia,
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Tris(pentafluorophenyl)silyl triflate: Synthesis and silylation of carbonyl compounds

Tris(pentafluorophenyl)silyl triflate (1) was prepared by protodesilylation of phenyl-, allyl-, and isopropenyloxytris(pentafluorophenyl)silyl derivatives and characterized by X-ray crystallography. This reagent was employed for the silylation of carbonyl compounds. Aldehydes and ketones afforded the corresponding silyl enol ethers in good yields, while silylation of esters and lactones was dependent on the reaction conditions and on the substrate. A mechanism accounting for the observed phenomena is proposed. Studies of the relative reactivities of 1 and trimethylsilyl triflate are also presented. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Extracurricular laboratory:new discovery of 3-Methyldihydrofuran-2(3H)-one

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Discovery of a phosphine-mediated cycloisomerization of alkynyl hemiketals: Access to spiroketals and dihydropyrazoles via tandem reactions

Reported here are details on the discovery of a phosphine-catalyzed isomerization of hemiketals and subsequent reactions of the cyclic keto enol ether products. The new cycloisomerization complements a previously reported amine-catalyzed process that gave oxepinones from the same hemiketal starting materials. In the absence of functionality (R2) on the cyclic keto enol ether, a rapid and facile dimerization occurs, giving spiroketal products. When the enone is substituted (i.e., R2 = Ph), the cyclic keto enol ether is sufficiently stable so that it can be isolated; it can then be further reacted in the same pot to provide the corresponding dihydropyrazoles. Both the spiroketal and dihydropyrazole products arise by a tandem reaction that begins with the novel cycloisomerization. The method allows for the rapid introduction of complexity in the products from relatively simple starting materials. It should find application in the synthesis of natural product-like molecules.

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Tetrahydrofuran – Wikipedia,
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Branched Diol Monomers from the Sequential Hydrogenation of Renewable Carboxylic Acids

A prominent challenge in replacing petrochemical polymers with bioderived alternatives is the efficient transformation of biomass into useful monomers. In this work, we demonstrate a practical process for the synthesis of multifunctional alcohols from five- and six-carbon acids using heterogeneous catalysts in aqueous media. Design of this process was guided by thermodynamic calculations, which indicate the need for two sequential high-pressure hydrogenations: one, reduction of the acid to a lactone at high temperature; two, further reduction of the lactone to the corresponding diol or triol at low temperature. For example, the conversion of mesaconic acid into (alpha or beta)-methyl-gamma-butyrolactone was achieved with 95 % selectivity at a turnover frequency of 1.2 min?1 over Pd/C at 240 C. Subsequent conversion of (alpha or beta)-methyl-gamma-butyrolactone into 2-methyl-1,4-butanediol was achieved with a yield of 80 % with Ru/C at 100 C. This process is an efficient method for the production of lactones, diols, and triols, all valuable monomers for the synthesis of bioderived branched polyesters.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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ALPHA7 NICOTINIC ACETYLCHOLINE RECEPTOR INHIBITORS

The present invention provides compounds and compositions, methods of making them, and methods of using them to modulate alpha7 nicotinic acetylcholine receptors and/or to treat any of a variety of disorders, diseases, and conditions. Provided compounds can affect, among other things, neurological, psychiatric and/or inflammatory systems.

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Tetrahydrofuran – Wikipedia,
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Synthesis of probes for the active site of leucine dehydrogenase

A series of novel 3-substituted 2-oxobutanoic acids were prepared and incubated with leucine dehydrogenase giving in one case both a kinetic resolution at C-3 and reductive amination of the ketone. This is the first example of an amino acid dehydrogenase catalysed kinetic resolution and reductive amination.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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One-step synthesis of O-benzyl hydroxamates from unactivated aliphatic and aromatic esters

We have developed a simple and high yielding one-step method for the synthesis of hydroxamate derivatives directly from a broad range of unactivated esters and the anion of O-benzyl-hydroxylamine generated in situ. The reaction takes place in minutes at -78 C. Very importantly, the method was successfully employed with enolizable esters, including chiral alpha-amino acid esters and peptides, with no trace of racemization/epimerization at the alpha carbon detected.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem