Ethyl 4-(4-oxopiperidin-1-yl)benzoate → Ethyl 4-(4-(2-(trifluoromethyl)benzylidene)piperidin-1-yl)benzoate

Participants

Reaction Steps

A suspension of 2-(trifluoromethyl)benzyl triphenylphosphonium bromide (prepared according to the procedure described in J. Chem. Soc. Perkin Trans. 11995, 18, 2293-2308) (0.737 g) in THF (10 mL) was treated with n-butyllithium (724 μL of a 1.6M solution in hexanes) at 0° C., treated with ethyl 4-(4-oxo-1-piperidinyl)benzoate (prepared according to the procedure described in Synthesis 1981, 606-608, 0.32 g), and gradually warmed to room temperature overnight. The reaction mixture was partitioned between ethyl acetate and saturated aqueous NH4Cl and the aqueous layer was extracted with ethyl acetate (2×). The combined organic layers were dried (MgSO4), filtered, and concentrated. The resulting residue was purified by silica gel chromatography eluting with 10% ethyl acetate in hexanes to give the desired product.

Provenance & Evidence