Citric Acid → (RS)-3-allyl-4-oxo-2-cyclopenten-1-yl (t-butyldimethylsilyl) ether

Participants

Reaction Steps

To a solution mixture of 8.8 g of (RS)-3-allyl-4-oxo-2-cyclopenten-1-ol, 100 ml of N,N-dimethylformamide and 4.75 g of imidazole was added t-butyldimethylsilyl chloride under ice-cooling, and the resulting mixture was stirred under ice-cooling for 8 hours. Then the reaction liquid was poured into ice-cooled 5% aqueous solution of citric acid and extracted two times with diethyl ether. The combined ether layer was washed successively with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 13.1 g of (RS)-3-allyl-4-oxo-2-cyclopenten-1-yl (t-butyldimethylsilyl) ether. Yield 81%

Provenance & Evidence