Hydrochloric Acid → HCID 57756001, compound

Participants

Reaction Conditions

Reaction Steps

(S)-binal-H (0.5 M tetrahydrofuran solution, 215 μl, 0.107 mmol) was added dropwise to a tetrahydrofuran solution (300 μl) of (12R,13S)-(E)-13-acetoxy-9-oxo-12-triisopropylsiloxy 10-octadecaenoic acid t-butyl ester (18) (18.7 mg, 0.033 mmol) at −78° C. over 5 minutes under the argon atmosphere, and the mixture was stirred at −78° C. for 1 hour and 30 minutes. Hydrochloric acid (1.0 N, 1 mL) was added to the reaction solution, and the mixture was extracted with chloroform (5 mL) three times. The organic layer was washed successively with 1.0 N sodium hydroxide (5 mL) and saturated brine (5 mL), dried over sodium sulfate, and concentrated. The resulting colorless oily crude product (20 mg) was separated and purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain (9S,12R,13S)-(E)-13-acetoxy-9-hydroxy-12-triisopropylsiloxy-10-octadecaenoic acid t-butyl ester (19) as a colorless oily substance (18.6 mg, 99%).

Provenance & Evidence