Pyridine → 2-[2-(5-Fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane

Participants

Reaction Steps

To a solution of 4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-trifluoromethylpentane-1,2-diol (8.15 g) and pyridine (21.2 mL) in 50 mL of methylene chloride (CH2Cl2) at 0° C.-5° C. was added dropwise methanesulfonyl chloride (2.63 mL). The mixture was warmed to room temperature, stirred overnight and methanol (80 mL) and K2CO3 (36.2 g) were added. The mixture was stirred 4 hours, diluted with diethyl ether, washed with water, dilute HCl, and brine, and dried over magnesium sulfate. Removal of the volatiles in vacuo provided a residue that was purified by flash silica gel chromatography using 5% EtOAc in hexanes as the eluent. The product-rich fractions were collected and the volatiles removed in vacuo to provide 2-[2-(5-fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane.

Provenance & Evidence