Ethanethiol → Methyl 3-[N-methyl-6-hydroxyindol-2-yl]-2,2-dimethylpropanoate

Participants

Reaction Steps

To a cold solution of 940 mg of the indole ester from Step B and 1.6 mL of ethanethiol in CH2Cl2 (50 mL) was added portion-wise 4.3 g of AlCl3. After complete addition, the mixture was stirred at R.T. for 2 h. The mixture was then cooled to 0 ° C. and carefully quenched with a solution of 0.5M Na,K tartrate (200 mL) and extracted with CH2Cl2. The organic layer was dried over Na2SO4 and evaporated to dryness to give a solid which was chromatographed on flash silica gel using ethyl acetate:hexane (30:70) as eluant to afford the title compound; m.p. 125°-126° C.

Provenance & Evidence