Sodium Bicarbonate → HCID 58026179, compound

Participants

Reaction Conditions

Reaction Steps

To 48 g (0.087 mol) of (R)-2-[2-(2-bromomethyl-4-fluorophenyl)-2-methylpropyl]-2-trifluoromethyloxirane in 1.3 L of DMF was added 36 g of sodium acetate (0.439 mol). The mixture was heated at 45° C. for 3 hours. The mixture was then cooled to room temperature and poured into 1.3 L of saturated aqueous sodium bicarbonate solution and extracted with 1800 mL of diethyl ether. The aqueous phase was filtered to remove a solid residue. The solid was washed with 1.3 L of diethyl ether. The organic phases were combined and washed with 2 L of brine and separated. The aqueous phase was extracted with 1800 mL of diethyl ether. The combined organic phases were dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude mixture was chromatographed on silica gel using 0-5% ethyl acetate/hexanes to afford 74.2 g (83%) of acetic acid 2-[1,1-dimethyl-2-((R)-2-trifluoromethyloxiranyl)ethyl]-5-fluorobenzyl ester.

Provenance & Evidence