Sodium hydride → HCID 68278821, compound

Participants

Reaction Steps

Sodium hydride (60% dispersion in oil, 0.081 g) was added to a solution of ethyl 2-(2-bromobenzenesulphonylamino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (Intermediate 39, 0.700 g) in anhydrous THF at 0° C. under nitrogen. The mixture was allowed to warm to room temperature and then stirred for 15 minutes. The mixture was then cooled to 0° C., 2-trimethysilylethoxymethyl chloride (0.360 ml) was added and the resultant mixture was stirred at room temperature for a further 64 hours. The reaction mixture was quenched by addition of saturated aqueous ammonium chloride (30 ml) and the product was extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane (0-20%) to give ethyl 2-[N-(2-bromobenzenesulphonyl)-N-(2-trimethylsilylethoxymethyl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (0.800 g) as a colourless oil.

Provenance & Evidence