Sodium Hydroxide → 2-(3,4-dichlorophenyl)-N-[trans-2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-cyclohexyl]-2-prop-2-ynyloxy-acetamide

Participants

Reaction Steps

To a stirred solution of 0.4 g (0.85 mmol) of 2-(3,4-dichlorophenyl)-2-hydroxy-N-[trans-2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-cyclohexyl]-acetamide, 0.5 ml of 30% aqueous sodium hydroxide solution and 5 mg of tetrabutylammonium bromide in 3 ml dichloromethane is added 0.18 g (0.85 mmol) of propynyl tosylate during 1 hour. Upon completion of the addition the reaction mixture is stirred for additional 16 hours at room temperature. The mixture is then extracted with dichloromethane. The organic extract is concentrated under reduced pressure to a residue, which was subjected to column chromatography on silica gel, with 1 :2 ethyl acetate/isohexane as the eluant to obtain 2-(3,4-dichlorophenyl)-N-[trans-2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-cyclohexyl]-2-prop-2-ynyloxy-acetamide.

Provenance & Evidence