Tetrahydrofuran → HCID 18509489, compound

Participants

Reaction Conditions

Reaction Steps

Compound 139 (4.21 g; 9.90 mmol) was dissolved in tetrahydrofuran (40 ml). While the solution was stirred at −78° C. under nitrogen atmosphere, n-butyl lithium in n-hexane (1.63 M: 6.1 ml; 9.94 mmol) was added dropwise. After 10 minutes, acetone (1.5 ml) was added dropwise thereto, and the mixture was gradually brought to room temperature. Saturated aqueous ammonium chloride solution was added dropwise to the mixture, and water was added thereto, 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=5:1→2:1), to thereby yield 3.11 g of the target compound as pale yellow oily matter (yield: 77.7%).

Provenance & Evidence