Water → HCID 67792972, compound

Participants

Reaction Steps

To a suspension of 60% sodium hydride (15 g) in dimethylformamide (30 ml) was added a N,N-dimethylformamide solution of 5-benzyloxyindole (5.0 g) at 0° C. After 15 minutes a solution of ethyl-3-chloropropionate (3.1 ml) in N,N-dimethylformamide was added dropwise and the reaction mixture stirred for a further 5 hours at ambient temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 15%-ethyl acetate in n-hexanes to yield the title product (6.81 g).

Provenance & Evidence