Methyl iodide → 2-ethyl-1H-indole

Participants

Reaction Steps

In an ice water bath, 2-methylindole (5 g, 38.1 mmol), 300 mL anhydrous diethyl ether, 2.4 M n-BuLi 47.5 mL (114 mmol), tert-butanol (8.5 g, 75.8 mmol) were added into a reaction vessel. Upon completion of addition, under protection of nitrogen, the reaction was stirred at room temperature for 0.5 h. Then the system was cooled to −70° C., and iodomethane (10.245 g, 72.2 mmol) was added dropwise. Upon completion of addition, it was reacted for 2 h maintaining this temperature. Then it was warmed up to −40° C. 2 mL water was added, and then warmed up to room temperature. The system was poured into water, adjusted to pH=6, extracted with diethyl ether, dried and rotate evaporated to dryness to obtain the product 3.74 g, at a yield of 67.7%.

Provenance & Evidence