Sodium hydride → HCID 90387563, compound

Participants

Reaction Steps

A solution of ethyl 2-methyl-1H-pyrrole-3-carboxylate (purchased from Beta Pharma Scientific, 9.91 g, 64.7 mmol) in tetrahydrofuran (200 mL) at 0° C. under N2 was treated portionwise with sodium hydride (dry, 95%) (2.06 g, 82 mmol). The resulting mixture was stirred for 20 minutes and treated with triisopropylchlorosilane (16.5 mL, 78 mmol). The mixture was stirred for 30 minutes, then the ice bath was removed. After warming to ambient temperature over 90 minutes, the mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous magnesium sulfate) filtered and concentrated. Purification by chromatography on a 330 g silica cartridge eluting with 0-20% ethyl acetate in hexane afforded the title compound.

Provenance & Evidence