Ethyl Acetate → HCID 22951509, compound

Participants

Reaction Steps

To a solution of 11 (945 mg, 1.55 mmol) in toluene (11 mL) at −78° C. (bath temperature) was added a 1.5 M solution of DIBAL-H in toluene (3.0 mL, 4.5 mmol). After 3.5 h, ethyl acetate (10 mL) was added, the mixture was warmed to room temperature, saturated sodium potassium tartarate (20 mL) was added, and the thick solution was stirred for 30 min to break the emulsion. The layers were separated, the aqueous phase was extracted with ethyl acetate (2×30 mL), the combined organic layers were dried (magnesium sulfate), filtered, concentrated, and chromatographed on a 13 cm tall×26 mm diameter silica gel column eluting with 40% ethyl acetate in hexane to afford 12 (968 mg, 100%).

Provenance & Evidence