Indole → 1H-Indole, 1-(1-methoxyethyl)-

Participants

Reaction Conditions

Reaction Steps

To a suspension of NaH (1.92 gm of a 60% dispersion in oil) in 75 mL of DMF was added indole (4.68 gm, 40 mmol) (Aldrich). The mixture was stirred for 15 minutes at 0° C., and 1-chloroethyl methylether (4 mL) was added dropwise. The resulting mixture was stirred at 0° C. for 1 hour and poured over ice/water, and extracted with toluene. The organic layer was dried over magnesium sulfate, and evaporated. The residue was purified by flash chromatography using EtOAc/hexanes to give 4 gm of 1-[1-methoxyethyl]indole. (Yield 58%).

Provenance & Evidence