Ethanol → (4S)-3,3-dimethyl-4-tetrahydropyranyloxy-1-hydroxymethylcyclohexene

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Reaction Steps

(4S)-3,3-dimethyl-4-tetrahydropyranyloxycyclohexene-1-carbaldehyde (8) (0.71 g, 2.98 mmoles) was dissolved in tetrahydrofuran (7 ml), and a 95% ethanol solution of sodium borohydride (0.38 g, 10 mmoles) was added dropwise over an ice bath. After the addition, the mixture was stirred for 2 hours at a temperature below 10° C. The solvent was evaporated under reduced pressure. The residue was diluted with water, and extracted twice with diethyl ether. The ethereal layer was dried over magnesium sulfate, filtered, concentrated, and purified by column chromatography (30 g of silica gel; n-hexane/ethyl acetate) to give 0.65 g (yield 91.3%) of a compound (9).

Provenance & Evidence