反应详情

Sodium hydride (1.23 g of a 60% dispersion in mineral oil) was added to dry N,N-dimethylformamide (100 ml), under an atmosphere of nitrogen. The mixture was cooled in an ice-bath, a solution of methyl 4-(5-formylindol-3-ylmethyl)-3-methoxybenzoate (9.0 g) in N,N-dimethylformamide (20 ml) added slowly, and the mixture stirred for 1 hr. Methyl iodide (4.34 g) was added slowly, stirring continued for 2.5 hr., then the mixture carefully acidified with hydrochloric acid (100 ml) to give an off-white precipitate which was purified by flash chromatography, eluting with 45:50:5 hexane:methylene chloride:ethyl acetate, to give a yellow oil which was crystallized from a mixture of ethyl acetate and hexane to give methyl 4-(5-formyl-1-methylindol-3-ylmethyl)-3-methoxybenzoate (7.6 g, 81%) as an off-white powder; mp 116°-118°; partial NMR(250 MHz, DMSO-d6): 3.80 (s, 3H, OCH3), 3.83(s, 3H, NCH3), 3.93(s, 3H, OCH 3), 4.11(s, 2H, ArCH2Ar'), 8.12(s, 1H, H4 -indole), 9.96(s, 1H, CHO).

1. temperatureThe mixture was cooled in an ice-bath
2. stirringstirring
3. waitcontinued for 2.5 hr
4. customto give an off-white precipitate which
5. customwas purified by flash chromatography
6. washeluting with 45:50:5 hexane
7. custommethylene chloride:ethyl acetate, to give a yellow oil which
8. customwas crystallized from a mixture of ethyl acetate and hexane