2-Methylindole → Sbb044946

Participants

Reaction Steps

To 2-methyl indole (1.69 g; 12.9 mmol) in 10 mL of THF at 0° C. was added MeMgBr 1.4M (12.9 mmol). After 30 min at 0° C. ZnCl2 1M (12.9 mL; 12.9 mmol) in THF was added and the reaction stirred for an other 30 min at r.t. Methyl bromoacetate (1.4 mL; 14.7 mmol) was added dropwise and left stirring for 48 h. The mixture was poured into aqueous NaHCO3, extracted with EtOAc (3×25 mL) and the combined organic extracts were washed with brine. The solution was dried over Na2SO4 and the solvent removed. Chromatography on silica gel (eluted with 5% EtOAc in hexane) yielded 1.13g (43%) of the title compound.

Provenance & Evidence