Hydrochloric Acid → HCID 86591007, compound

Participants

Reaction Conditions

Reaction Steps

(R)-binal-H (0.5 M tetrahydrofuran solution, 232 μL, 0.116 mmol) was added dropwise to a tetrahydrofuran solution (0.35 mL) of (12R,13S)-(E)-13-acetoxy-9-oxo-12-triisopropylsiloxy-10-octadecaenoic acid t-butyl ester (18) (20.5 mg, 0.0352 mmol) synthesized in Example 4-4) 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, and the mixture was extracted with chloroform (5 mL) three times. The organic layers were combined, washed successively with 1.0 N sodium hydroxide (5 mL×3) and saturated brine (5 mL), dried over sodium sulfate, and concentrated. The resulting colorless oily crude product (21 mg) was separated and purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain (9R,12R,13S)-(E)-13-acetoxy-9-hydroxy-12-triisopropylsiloxy-10-octadecaenoic acid t-butyl ester (21) (20.3 mg, 99%)

Provenance & Evidence