Indole → Methyl 3-indoleglyoxylate

Participants

Reaction Conditions

Reaction Steps

A solution of indole (2.0 g, 1.70 mmol) in Et2O (20 mL) was cooled to 0°-5° C. under N2 and oxalyl chloride (1.5 mL 1.70 mmol) was added dropwise at <5° C. The resultant yellow slurry was stirred 30 min. in the ice bath and was then cooled to -65° C. and a 25% wt. solution of sodium methoxide (7.8 mL, 3.4 mmol) was slowly added at <-58° C. The reaction was then allowed to warm to room temperature, water was added (10 mL), and the resultant mixture filtered. The solid was dried at room temperature to give 3.21 g (93%) of the titled compound. NMR. MS (FD) m/z=203 (M+, 100%). Analytical calculated for C11H9NO3C, 65.02; H, 4.46; N, 6.89. Found C, 64.93; H, 4.25; N, 7.03.

Provenance & Evidence