Acetone → HCID 18509437, compound

Participants

Reaction Conditions

Reaction Steps

Compound 85 (1.42 g; 3.94 mmol) was dissolved in tetrahydrofuran (20 ml). While the solution was stirred at −75° C. under nitrogen atmosphere, n-butyl lithium in n-hexane (1.56 M: 2.5 ml; 3.94 mmol) was added dropwise. The mixture was stirred for 15 minutes, and acetone (2 ml) was added dropwise thereto. The resultant mixture was brought to room temperature over 2 hours, and the reaction was stopped by dropwise addition of saturated aqueous ammonium chloride solution, followed by extraction with diethyl ether (100 ml). The organic layer was washed with saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1→4:1), to thereby yield 0.41 g of the target compound as yellow oily matter (yield: 30.6%).

Provenance & Evidence