反应详情

A solution of 6-hydroxymethyl-1H-indole-1-carboxylic acid, 1,1-dimethylethyl ester (Example 31; 5.10 g, 20.6 mmol) and o-iodoxybenzoic acid (prepared by the literature procedure: Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019-8022; 8.00 g, 28.6 mmol) in dimethylsulfoxide (25 mL) was stirred at room temperature for 4 h. Water (200 mL) was added and the solution was extracted with dichloromethane (3×100 mL). The combined extracts were washed with brine (200 mL), dried (MgSO4), filtered, evaporated in vacuo. The residual material was chromatographed over silica gel (20-30% ethyl acetate/hexanes) to give 6-formyl-1H-indole-1-carboxylic acid, 1,1-dimethylethyl ester (2.14 g, 42% yield) as a colorless solid.

1. extractionthe solution was extracted with dichloromethane (3×100 mL)
2. washThe combined extracts were washed with brine (200 mL)
3. dry with materialdried (MgSO4)
4. filtrationfiltered
5. customevaporated in vacuo
6. customThe residual material was chromatographed over silica gel (20-30% ethyl acetate/hexanes)