Sodium hydride → 4-Tert-butyl-2-[5-(3-cyanophenylmethoxy)benzofuran-2-yl]thiazole

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Reaction Steps

To a cooled solution of 4-tert-butyl 2-(5-hydroxybenzofuran-2-yl)thiazole (0.33 g) in N,N-dimethylformamide (5 ml), sodium hydride ((60% in mineral oil) 55 mg) was added below 10° C. After being stirred for 10 minutes, 3-bromomethylbenzonitrile (0.26 g) was added to the mixture. After being stirred at ambient temperature for 2 hours, the resulting mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure to give a syrup. The syrup was crystallized with diisopropyl ether and filtered to give crystals of 4-tert-butyl-2-[5-(3-cyanophenylmethoxy)benzofuran-2-yl]thiazole (0.38 g).

Provenance & Evidence