tert-Butanol → Boc-indole

Participants

Reaction Steps

1.00 g (6.21 mmol) indole-2-carboxylic acid is dissolved in 15 ml absolute THF, mixed with 1.01 g (6.23 mmol) N,N-carbonyldiimidazole and stirred at room temperature for 1 hour. Thereafter, 0.77 g (6.86 mmol) potassium-tert-butylate and 9.12 g (123 mmol) tert-butanol are added. Following heating under reflux for 6 hours, quenching using 5 ml water, filtrating off, rinsing with THF, drying on sodium sulfate and concentration on the rotary evaporator, a brown solid is obtained as the crude product. Preliminary purification by means of column chromatography on silica gel using a short column with petroleum ether/ethyl acetate 95:5 leaves a white solid which is purified on silica gel by means of column chromatography (flow agent: petroleum ether/ethyl acetate 98:2) and yields the product as a white solid.

Provenance & Evidence