Sodium borohydride → HCID 19385051, compound

Participants

Reaction Conditions

Reaction Steps

NaBH4 (210 mg, 5.54 mmol) was added in portions to a solution of 4-(1-hydroxytridecyl)-5-hydroxy-5-methyl-2-furanone (586 mg, 1.85 mmol) in anhydrous ethyle glycol dimethyl ether (60 mL) at 0° C. under argon. After stirring for 3 hours at 0° C. the reaction was quenched with HCl (6N) to pH2 and extracted with ethyl acetate. The combined organic fractions were washed with a saturated solution of aqueous sodium bicarbonate, H2O and brine. Evaporation of the dried (magnesium sulfate) extracts gave an oil which was purified by flash chromatography on silica using 30% ethyl acetate/hexane to give the title compound as a mixture of diastereomers. Recrystallization from diethyl ether/hexane gave a single diastereomer.

Provenance & Evidence