Thionyl Chloride → (2-Cyclopentyl-5-methyl-1,3-oxazol-4-yl)methanol

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Reaction Steps

A mixture of 2-cyclopentyl-5-methyl-4-oxazolecarboxylic acid (7.0 g) and thionyl chloride (14 ml) was refluxed with stirring for 40 minutes. The thionyl chloride was completely distilled off and the residue was dissolved in dimethoxyethane (70 ml). The solution was added dropwise to a mixture of sodium borohydride (2.7 g) and dimethoxyethane (50 ml) with ice-cooling and stirring. The mixture was stirred for 30 minutes, adjusted to pH 2 with 2N hydrochloric acid and refluxed for 30 minutes. The solvent was then distilled off and aqueous sodium hydrogen carbonate was added. The mixture was extracted with ethyl ether and the ethyl ether layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by chromatography using silica gel (75 g) [eluent: hexane-acetone (7:3)] to give 2-cyclopentyl-4-hydoxymethyl-5-methyloxazole as an oil; yield 4.0 g (61.5%).

Provenance & Evidence