反应详情

To a solution stirred under nitrogen at room temperature of 5.0 mL methanol in 15.0 mL ether was added 0.84 g 60% sodium hydride (0.021 mol) in small portions (sodium hydride was used because metallic sodium was not available). After the addition was complete, the nearly clear and colorless solution was stirred for 5 minutes. To it was then added 1.3 g dimethyl malonate, giving a slightly cloudy colorless solution. To this was rapidly added a suspension of 3.1 g 1,2-bis(bromomethyl)3-nitrobenzene, which immediate gave a precipitate suspended in a dark green solution. This was removed by filtation and the filtrate was concentrated. The residue was purified on silica (20%-100% CH2Cl2 in hexanes) to give 1.93 g off-white solid (67%).

1. additionAfter the addition
2. customgiving a slightly cloudy colorless solution
3. additionTo this was rapidly added
4. customimmediate gave a precipitate
5. customThis was removed by filtation
6. concentrationthe filtrate was concentrated
7. customThe residue was purified on silica (20%-100% CH2Cl2 in hexanes)