Carbon Tetrachloride → HCID 131728921, compound

Participants

Reaction Steps

Triphenylphosphine (1.85 g, 7.05 mmol) and carbon tetrachloride (0.78 mL, 8.14 mmol) were added to a dimethylformamide solution (8.0 mL) of tert-butyl(±)-[(1R,5R,6R)-3-(hydroxymethyl)-6-(nitromethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetate (807 mg, 2.71 mmol), and the mixture was stirred at room temperature for 1 hour. To the reaction solution, water was added, followed by extraction with diethyl ether. The organic layer was washed with saturated saline and then dried over anhydrous sodium sulfate. The residue was filtered and concentrated under reduced pressure. Then, the obtained crude product of tert-butyl(±)-[(1R,5R,6R)-3-(chloromethyl)-6-(nitromethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetate was dissolved in dimethylformamide (10 mL). To the solution, sodium thiomethoxide (570 mg, 8.14 mmol) was added with stirring at 0° C., and the mixture was stirred at this temperature for 4 hours. The reaction solution was diluted with ethyl acetate and separated into aqueous and organic layers. The organic layer was washed with a 1 M aqueous sodium hydroxide solution, water, and saturated saline and then dried over anhydrous sodium sulfate. The residue was filtered and concentrated under reduced pressure. Then, the obtained crude product was purified by silica gel column chromatography to obtain the compound of interest as an oil substance (632 mg, 71%).

Provenance & Evidence