反应详情

A solution of borane dimethyl sulfide complex (2M in THF, 6.50 mL) was added portionwise over 5 minutes to a solution of 5-(carboxymethyl)-2-chlorobenzoic acid [Aromatic Intermediate 7, step b] (1.37 g) in dry THF (20 mL) at room temperature. The resulting effervescing solution was stirred at room temperature for 1.5 hours, then heated to reflux for 1 hour. The cooled mixture was quenched by the portionwise addition of methanol (5 mL) over 5 minutes. The solution was stirred at room temperature for 2 hours and then purified by flash chromatography on silica eluted with 5% methanol in dichloromethane to afford the subtitled compound as a colourless oil. Yield 0.933 g.

1. temperatureheated
2. temperatureto reflux for 1 hour
3. customThe cooled mixture was quenched by the portionwise addition of methanol (5 mL) over 5 minutes
4. stirringThe solution was stirred at room temperature for 2 hours
5. custompurified by flash chromatography on silica
6. washeluted with 5% methanol in dichloromethane