Sodium hydride → HCID 67309804, compound

Temperature

25 °C

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.

1. additionAfter the addition
2. stirringstirred overnight
3. customThe reaction was quenched with saturated aqueous ammonium chloride solution (30 mL)
4. extractionwas extracted with ether (4×50 mL)
5. washThe combined organic layer was then washed with half-saturated brine
6. dry with materialdried over Na2SO4
7. filtrationAfter filtration and concentration
8. customthe residue was purified on silica gel (20 percent acetone/hexane)

ORD record

ord-aca6a07f3924494a8e12824cd011418b

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08008487B2