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

Participants

Reaction Conditions

Reaction Steps

A solution of 1.15 g (2.43 mmol) of methyl {1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene}(3,5-difluorophenyl)acetate (Preparation 5) in 10 mL of dry ethyl ether was cooled to −78° C. under nitrogen. Dropwise, 3.1 mL of a 1M solution of methyllithium in ether was added. After 30 minutes, another 3.1 mL of the 1M solution of methyllithium in ether was added dropwise and the solution was stirred at −78° C. for 30 min. The reaction was quenched by addition of water and the mixture was partitioned between ether and water. The aqueous extract was washed with ether and the combined organic layers were washed with brine, dried over Na2SO4, and concentrated. The residue was purified by chromatography on a Waters RCM column (5 micron silica gel, 20 mm×10 cm) using a 2:1 mixture of hexane and 5:4:1 hexane-methyl tert-butyl ether-acetonitrile. Homogenous fractions were pooled and concentrated to afford the title compound; 1NMR (CDCl3) δ 1.35 (s, 3H), 3.49 (m, 2H), 4.09 (m, 2H), 4.46 (s, 1H), 6.68 (m, 1H), 6.70 (m, 1H), 7.26 (m, 4H), 7.34 (m, 4H); Mass Spectrum: m/e=474 (M+1 35Cl, 35Cl) and 476 (M+1 35Cl, 37Cl).

Provenance & Evidence