Hexane → 1-Benzyloxycarbonyl-3-[2-[2-(4-chlorophenyl)-4-methylthiazol-5-yl]ethenyl]piperidine

Participants

Reaction Conditions

Reaction Steps

In an argon atmosphere, a solution of 1.59 mol/Ln-butyl lithium in hexane (2.03 mL, 3.23 mmol), chilled to −78° C., was added to a suspension of [2-(4-chlorophenyl)-4-methylthiazol-5-yl]methyltriphenylphosphonium iodide (1.80 g, 2.94 mmol) in tetrahydrofuran (20 mL). The reaction mixture was stirred for 1 hour as it warmed from −78° C. to room temperature. Subsequently, the mixture was chilled again to −78° C. and 1-benzyloxycarbonyl-3-formylpiperidine (727 mg, 2.94 mmol) in tetrahydrofuran (5 mL) was added. The mixture was stirred at −78° C. for 1 hour and at room temperature for the subsequent 6 hours. Subsequently, water was added and the mixture was extracted with ethyl acetate and washed with brine. The washed product was dried over magnesium sulfate and the solvent was evaporated. Purification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=20:1->5:1) gave 1.16 g (87%) of the desired compound as a yellow oil.

Provenance & Evidence