1,2-Dimethoxyethane → HCID 10335035, compound

Participants

Reaction Steps

To a mixture of sodium hydride (60% in mineral oil, 128 mg, 3.2 mmol) in ethylene glycol dimethyl ether (4 mL) was added dropwise at 0° C. a solution of triethyl phosphonocrotonate (800 mg, 3.2 mmol) in ethylene glycol dimethyl ether (2 mL). The mixture was stirred at room temperature for 45 min. A solution of 5-dimethylamino-benzo[b]thiophene-2-carboxaldehyde (596 mg, 2.9 mmol) in ethylene glycol dimethyl ether (5 mL) was added in dropwise manner. The mixture was stirred at reflux for 90 min, cooled to room temperature and diluted by addition of ethyl acetate (50 mL). The mixture was washed with water (3×25 mL) and brine (25 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give an oil, that was purified by flash chromatography (10:90:1 ethyl acetate:40-60° C. petroleum ether:triethylamine) to give a solid that was recrystallised from ethanol to give the title compound (567 mg, 65%) as a solid, mp 140-142° C.

Provenance & Evidence