Water → Tert-butyl 6-formyl-1H-indole-1-carboxylate

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Reaction Steps

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.

Provenance & Evidence