Ammonium Chloride → HCID 59131023, compound

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (2.5M in hexanes) (100 mL, 250 mmol) was added dropwise to a stirred solution of (S)-(−)-4-benzyl-2-oxazolidinone (43.55 g, 250 mmol) in anhydrous tetrahydrofuran (350 mL) at 0° C. The resulting solution was cooled to −78° C. for 30 minutes and added dropwise to a stirring solution of tert-butyl (2E)-3-(2,4-difluorophenyl)prop-2-enoyl carbonate, from preparation 27 via cannula at −78° C. The resulting suspension was allowed to warm to 0° C. and saturated ammonium chloride solution (75 mL) was added, followed by water (50 mL). The phases were separated and the aqueous layer was extracted with ethyl acetate (2×300 mL). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated in vacuo to give a slurry. Cyclohexane (178.5 mL) and tert-butyl methyl ether (126 mL) were added to the slurry and the mixture was stirred for 2 hours at room temperature. The resulting white solid was collected via filtration and dried in a vacuum oven at 40° C. to give the desired product, 45.48 g (61%).

Provenance & Evidence