Sodium hydride → HCID 67309804, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of trans-1-[2-(hydroxymethyl)cyclopropyl]ethanone (3.4 g, 30 mmol) (prepared as disclosed in Cossy, J.; Blanchard, N.; Meyer, C. Eur. J. Org. Chem. 2001, 339) in anhydrous DMF (60 mL) was added sodium hydride (60 percent dispersion in oil, 1.4 g, 36 mmol) in portions under N2 at 0° C. After the addition was complete, the mixture was stirred for 25 minutes and 4-methoxybenzyl chloride (5.2 g, 33 mmol) was added in one portion. The reaction was then allowed to warm to approximately 25° C. and stirred overnight. The reaction was quenched with saturated aqueous ammonium chloride solution (30 mL) followed by dilution with water and was extracted with ether (4×50 mL). The combined organic layer was then washed with half-saturated brine and dried over Na2SO4. After filtration and concentration, the residue was purified on silica gel (20 percent acetone/hexane) to give 4.1 g of product as a colorless oil in 58 percent yield.

Provenance & Evidence