Carbon Dioxide → HCID 18509451, compound

Participants

Reaction Steps

Compound 78 (2.26 g; 6.53 mmol) was dissolved in tetrahydrofuran (25 ml), and the solution was cooled to −75° C. by use of a mixture of dry ice and acetone solvent under nitrogen atmosphere. n-butyl lithium in n-hexane (1.56 M: 4.2 ml; 6.53 mmol) was slowly added dropwise to the mixture, and the resultant mixture was stirred for 15 minutes. Subsequently, N,N-dimethylformamide (0.95 g; 13.1 mmol) was added dropwise to the mixture, and the resultant mixture was gradually brought to room temperature. Reaction was stopped by dropwise addition of saturated aqueous ammonium chloride solution, followed by extraction with ether (100 ml). The organic layer was washed with saturated aqueous sodium bicarbonate solution and then with saturated brine, and dried over anhydrous 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), to thereby yield 0.59 g of the target compound (yield: 30.6%).

Provenance & Evidence