1,1-Dimethylethyl 6-formyl-2,2-dimethyl-1,3-dioxane-4-acetate → 1,1-Dimethylethyl 6-[4,4-bis(4-fluorophenyl)-3-trifluoromethyl-1,3-butadienyl]-1,3-dioxane-4-acetate

Participants

Reaction Steps

Butyl lithium(1.2 mL of 2.5M solution, 3.0 mmol) was added to a solution of dimethyl [3,3-bis(4-fluorophenyl)-2-trifluoromethyl-2-propen-1-yl]phosphonate in 20 mL tetrahydrofuran at -70° C. followed by immediate addition of 1,1-dimethylethyl 6-formyl-2,2-dimethyl-1,3-dioxane-4-acetate (0.9 g, 3.6 mmol). The solution was allowed to gradually warm to room temperature and then stirred for 14 hours. The reaction was quenched with saturated ammonium chloride solution and the mixture extracted with diethyl ether. The extracts were dried and concentrated in vacuo. The residue was purified by chromatography on silica eluting with 10% ethyl acetate in hexane to give 0.7 g of the title compound as an oil. MS(CI): m/e =538 for M+ of C29H31F4O4.

Provenance & Evidence