Sodium hydride → HCID 19434009, compound

Participants

Reaction Steps

The product from Step F (0.3 g, 0.88 mmol) was added to a suspension of sodium hydride (0.05 g of a 60% suspension in mineral oil, rinsed once with hexane, 1.25 mmol) in DMF (5 mL) at 0° C. The cooling bath was removed and the mixture was stirred for one hour at which point 2-bromoethyl methyl ether (0.09 mL, 0.97 mmol) was added. The mixture was stirred for 18 hr at room temperature, water was added and the mixture extracted with ethyl acetate (3×3 mL). The combined extracts were washed with water (10 mL), dried (MgSO4) and evaporated to provide an oil which was purified by column chromatography (silica, hexane/ethyl acetate gradient) to give the desired product as an oil (0.35 g, 100%) which was used in the next reaction.

Provenance & Evidence