Citric Acid → HCID 22908403, compound

Participants

Reaction Steps

After 10 g of(RS)-4-hydroxy-3-methyl-2-ethylcyclopent-2-en-1-one and 5.78 g of imidazole were dissolved in 100 ml of dry dimethylformamide, 11.91 g of t-butyldimethylchlorosilane was added to the solution at an ambient temperature. After stirring at an ambient temperature for 14 hours, the reaction solution was added to 5% aqueous citric acid under ice-water cooling, and extracted three times with diethyl ether. The combined organic layer was washed successively with a saturated sodium hydrogencarbonate solution and a saturated sodium chloride solution, and dried with anhydrous magnesium sulfate. After removal of the solvent under reduced pressure, the residue was subjected to silica gel column chromatography to yield 14.231 g of (RS)-4-t-butyldimethylsilyloxy-3-methyl-2-ethylcyclopent-2-en-1-one. Yield 82% (Eluent: n-hexane/ethyl acetate=5/1 (v/v))

Provenance & Evidence