Acetone → HCID 18509448, compound

Participants

Reaction Conditions

Reaction Steps

Compound 16 (2.24 g; 6.70 mmol) was dissolved in tetrahydrofuran (25 ml), and the solution was cooled to −78° C. under nitrogen atmosphere. n-butyl lithium in n-hexane (1.56 M: 4.3 ml; 6.70 mmol) was added dropwise to the resultant mixture, and stirred for 15 minutes. Acetone (3 ml) was added dropwise to the mixture, and brought to room temperature over 3 hours, followed by stirring for 1 hour at room temperature. Reaction was stopped by dropwise addition of saturated aqueous ammonium chloride solution, followed by extraction with diethyl ether (50 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=5:1), to thereby yield 1.13 g of the target compound (yield: 53.8%).

Provenance & Evidence