Acetic Acid → HCID 10962242, compound

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (5.08 g; 40 mmoles) and 60 ml of dichloromethane were taken into a nitrogen-purged 500 ml eggplant-shaped flask, and cooled to -50° C. A solution of 6.24 g (80 mmoles) of dimethyl sulfoxide in 20 ml of dichloromethane was added, and the mixture was stirred for 30 minutes. A solution of 9.09 g (17.9 mmoles) of (1R,2R,3R,4S)-1-t-butyldimethylsilyloxy-2-[(E,3S)-3-t-butyldimethylsilyloxy-1-octenyl]-4-hydroxymethyl-3-(2-propynyl)cyclopentane (32) in 40 ml of dichloromethane was added, and the mixture was stirred at -50° C. for 30 minutes. Subsequently, 10.1 g (100 mmoles) of triethylamine was added, and the mixture was stirred at -50° C. for 30 minutes. Acetic acid (7.2 g; 120 mmoles) was added, and the mixture was stirred for 10 minutes. The reaction mixture was poured into saturated aqueous ammonium chloride solution and extracted with dichloromethane. The organic layer was washed successively with saturated aqueous potassium hydrogensulfate and saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 9.05 g (yield of the crude product 100%) of (1R,2R,3R,4S)-1-t-butyldimethylsilyloxy-2-[(E,3S)-3-t-butyldimethylsilyloxy-1-octenyl]-4-formyl-3-(2-propynyl)cyclopentane (20).

Provenance & Evidence