Water → HCID 22405272, compound

Participants

Reaction Steps

To a solution of ethyl diethylphosphonoacetate (6.10 g) in tetrahydrofuran (50 ml) was added sodium hydride (60% in oil, 599 mg) and the solution was stirred at ambient temperature for 30 minutes. To the solution was added a solution of 1-(4-nitrobenzoyl)-2,3,4,5-tetrahydro -1H-1-benzazepine (3.10 g) in tetrahydrofuran (10 ml) dropwise and the mixture was stirred at ambient temperature for 5 hours. The solution was poured into water and the aqueous solution was extracted with ethyl acetate. The organic phase was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated in vacuo and the crude product was purified by silica gel column (100 g, 1% methanol in chloroform) to give 5-ethoxycarbonylmethylene-1-(4-nitrobenzoyl) -2,3,4,5-tetrahydro-1H-1-benzazepine (689 mg) and 5-ethoxycarbonylmethyl-1-(4-nitrobenzoyl)-2,3-dihydro -1H-1-benzazepine (905 mg).

Provenance & Evidence