Hydrochloric Acid → HCID 11377032, compound

Participants

Reaction Conditions

Reaction Steps

(S)-binal-H (0.5 M tetrahydrofuran solution, 335 μL, 0.167 mmol) was added dropwise to a tetrahydrofuran solution (500 μL) of (12S,13S)-(E)-12,13-di-tert-butyldimethylsiloxy-9-oxo-10-octadecaenoic acid t-butyl ester (11) (31.1 mg, 0.0508 mmol) at −78° C. over 5 minutes under the argon atmosphere, and the mixture was stirred at −78° C. for 1 hour. Hydrochloric acid (1.0 N, 1 mL) was added to the reaction solution, the mixture was extracted with chloroform (5 mL) three times, and the organic layer was washed successively with 1.0 N sodium hydroxide (5 mL×3), and saturated brine (5 mL), dried over magnesium sulfate, and concentrated. The resulting colorless oily crude product (32 mg) was separated and purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain (9S,12S,13S)-(E)-12,13-di-tert-butyldimethylsiloxy-9-hydroxy-10-octadecaenoic acid t-butyl ester (12) as a colorless oily substance (31.0 mg, 99%).

Provenance & Evidence