反应详情

To a solution of 1.6M n-butyl lithium in n-hexane (16.5 m,) in toluene (20 ml) at -20°, under nitrogen, was added a solution of 2-bromo-6,7,8,9-tetrahydro-3-methyl 5-H-cyclohepta[b]pyridine (6 g, 0.025 m) in toluene (30 ml). The reaction mixture was kept at -20° C. for 0.25 hours and then blown over into a cooled solution (-20° C.) of 3-methoxybenzaldehyde (3.7 g) in toluene (30 ml) and allowed to warm up to room temperature. Water was added and the organic phase separated and treated with 2N hydrochloric acid. A precipitate formed and this was collected by filtration and treated with sodium carbonate solution, then chloroform. The organic phase was washed with water, dried (MgO4) and evaporated. Trituration with diethyl ether gave 1-(6,7,8,9-tetrahydro-3-methyl-5H-cyclohepta[b]pyrid-2-yl)-1-(3-methoxyphenyl)methanol (4.42 g, 59%) m.p. 104°-6° C.

1. customthe organic phase separated
2. additiontreated with 2N hydrochloric acid
3. customA precipitate formed
4. filtrationthis was collected by filtration
5. additiontreated with sodium carbonate solution
6. washThe organic phase was washed with water
7. customdried (MgO4)
8. customevaporated