Diethyl Ether → 1-{1-[(4-Chlorophenyl)(phenyl)methyl]azetidin-3-ylidene}-1-(3,5-difluorophenyl)-2-methylpropan-2-ol

A solution of 0.044 g (0.1 mmol) of methyl {1-[(4-chlorophenyl)(phenyl)methyl]azetidin-3-ylidene}(3,5-difluorophenyl)acetate in 5 mL dry ether was cooled to −78° C. under nitrogen. To this was added 0.45 mL of a 1M solution of methyllithium and the resulting solution was stirred at −78° C. for 30 minutes. A second aliquot of 0.45 mL of a 1M solution of methyllithium was added and the solution was allowed to warm to −60° C. After 1 h, the reaction was quenched by addition of 5 mL water and the layers were separated. The aqueous layer was washed with three 10 mL portions of ethyl acetate and the organic extracts were combined, dried over Na2SO4 and concentrated. The residue was purified by reverse phase chromatography (Waters Xterra C18, 19 mm×10 mm) using a gradient of CH3CN—H2O-Et3N (20:80:0.1 to 60:40:0.1). Homogenous fractions were pooled and concentrated to afford the title compound; 1NMR (CDCl3) δ 1.37 (s, 6H), 3.52 (m, 2H), 4.12 (m, 2H), 4.50 (s, 1H), 6.68-6.76 (m, 3H), 7.22-7.42 (m, 9H); Mass Spectrum: m/e=440 (M+1 35Cl and 442 (M+1 37Cl).