Nitrogen → HCID 86723000, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (−78° C.) mixture of Ph3PCH2Br (5.42 g, 14.88 mmol) in THF (25 mL) was added KOtBu (1M in THF, 17.05 mL, 17.05 mmol) dropwise under N2. The resulting mixture was stirred at 0° C. for 1 h and warmed to rt for another 1.5 h. The reaction mixture was then cooled to −40° C., added a solution of 4-(2-(benzyloxy)ethyl)cyclohexanone (1.8 g, 7.75 mmol) in THF (15 mL) dropwise. The mixture was then stirred at rt overnight and quenched by brine, extracted with EtOAc, dried over Na2SO4. Purification by flash column chromatography (eluent: 20% EtOAc in hexanes to 30%) gave the titled product (1.77 g, 99%). LC/MC: 231.1 (MH)+.

Provenance & Evidence