Dimethylformamide → HCID 86753760, compound

Participants

Reaction Conditions

Reaction Steps

Combine sodium hydride (0.66 g, 60% in oil, 13.1 mmol) and dimethylformamide [50 mL). Cool to 0° C. using an ice-bath. Add t-butyl (5-methoxy-2-methyl-indol-3-yl]-acetate (3 g, 10.9 mmol). Stir until gas evolution ceases. Add 4-methoxybenzoyl chloride (2.23 g, 13 mmol). Warm to ambient temperature. After 18 hours, add water. Partition the reaction mixture between ethyl acetate and water. Separate the organic layer and extract with a saturated sodium chloride solution. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 1/4 ethyl acetate hexane to give the title compound.

Provenance & Evidence