Tetrahydrofuran → 4-allyl-5-hydroxy-N-(4-fluorobenzyl)indole

Participants

Reaction Steps

To a solution of sodium hydride (60%, 140 mg, 3.47 mmol) in 4 mL tetrahydrofuran (THF) was added 5-allyloxyindole (Step A; 0.5 g, 2.89 mmol) in 1 mL and the mixture was stirred for 1 hour at ambient temperature. 4-fluorobenzyl bromide (0.43 mL, 3.32 mmol) was added and the reaction stirred 18 hours. The reaction was then quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over magnesium sulfate, filtered through a short pad of silica and used directly in the next step.

Provenance & Evidence