Sodium borohydride → HCID 19385048, compound

Participants

Reaction Steps

NaBH4 (25 mg, 0.67 mmol) was added to a solution of 4-(1-acetoxytridecyl)-3-methyl-5-hydroxy-2(5-H)-furanone (157 mg, 0.44 mmol) in anhydrous THF (20 mL) at room temperature under argon. After 2 hours aqueous HCL (1N) was added carefully until pH2 was reached and the resulting mixture was stirred an additional 1 hour. This mixture was extracted with ethyl acetate and the combined organic fractions were washed with 5% sodium bicarbonate 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. Fractions with Rf of about 0.45 on evaporation afforded the title compound.

Provenance & Evidence