Sodium hydride → HCID 90387295, compound

Participants

Reaction Steps

A solution of Example 93b (8.826 g, 48.7 mmol) in tetrahydrofuran (325 mL) was chilled in an ice bath and treated with sodium hydride (dry, 95%) (2.454 g, 97 mmol) added portionwise over 15 minutes. The mixture was stirred under N2 for 10 minutes and treated with (2-(chloromethoxy)ethyl)trimethylsilane (12 mL, 67.8 mmol), then stirred for 50 minutes. The reaction vessel was removed from the ice bath and allowed to warm to ambient temperature. The reaction mixture was carefully quenched with 200 mL of saturated aqueous ammonium chloride, reduced in volume by rotovap and shaken in a separatory funnel with 350 mL each of ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous magnesium sulfate), filtered and concentrated. The crude material was chromatographed on a 330 g silica gel cartridge eluting with 0-50% ethyl acetate/heptane to provide the title compound.

Provenance & Evidence