2-Methylindole → Ethyl 2-(1H-indol-2-yl)acetate

Participants

Reaction Steps

2-Methylindole (1.7 g, 13 mmol) in 130 mL Et2O was treated with nBuLi (1.6M in hexane, 24.4 mL, 39 mmol) and KOtBu (1.0M in THF, 26 mL, 26 mmol) at RT for 40 min, then diethylcarbonate (3.15 mL, 26 mmol) was added. After 1 h the reaction was quenched with water, adjusted to pH 7 with 6N HCl, extracted with EtOAc, then the organic layer was washed with water and brine, dried (MgSO4), and concentrated. Flash chromatography (silica 10% then 20% EtOAc/hexane) provided 4-1 as a brown oil. Rf 0.33 (silica, 20% EtOAc/hexane).

Provenance & Evidence