Ethanethiol → Methyl 3-[5-hydroxyindol-2-yl]-2,2-dimethylpropanoate

Participants

Reaction Steps

To a solution of the compound from step A (25.50 g, 73 mmol) in CH2Cl2 (250 ml) at 0° C. was added AlCl3 (87.70 g, 9 mol eq.) portion-wise. When the addition was complete, the ice-bath was removed and the mixture was stirred at RT for 3 hours. EtSH (27 ml, 5 mol eq.) was added and the resulting mixture was stirred for a further 5 hours. It was then slowly poured onto an ice-cold 1M solution of Na, K tartrate. The product was extracted into CH2Cl2 (×2) and the organic phase was washed with aq. NaCl (×3). Conventional work-up followed chromatography on silica gel using EtOAc/hexane 1:5 to 3:2 afforded 13.60 g of-the title compound, 75% yield.

Provenance & Evidence