Water → HCID 69481139, compound

Participants

Reaction Steps

Triphenyl-(4-trifluoromethylbenzyl)-phosphonium bromide (3.00 g, 5.98 mmol) was dissolved in DMSO (50 ml). To the solution, sodium hydride (0.239 g, 5.98 mmol) was added with cooling on ice-bath followed by stirring at room temperature for 1 hour. To the solution, a solution of benzyl 4-formyloxypiperidine-1-carboxylate (1.497 g, 5.69 mmol) in DMSO (10 ml) was added dropwise followed by stirring at 60° C. for 7 hours. The reaction mixture was added water and extracted with ethyl acetate twice. The organic phases were combined, washed with water and a saturated saline solution, dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) and then purified by silica gel column chromatography (methylene chloride/ethyl acetate=9/1) to afford benzyl 4-[2-(4-trifluoromethylphenyl)-vinyloxy]piperidin-1-carboxylate as a colorless oil.

Provenance & Evidence