Ammonium Chloride → 1-(Bicyclo[2.2.1]heptan-2-yl)-2-methylprop-2-en-1-ol

Participants

Reaction Steps

Bicyclo[2.2.1]heptane-2-carbaldehyde (47 g, 378 mmol) in THF (25 ml) was added dropwise to isopropenylmagnesium bromide (0.5 molar in THF, 860 ml, 430 mmol) at −78° C. (slurry at this temperature) under nitrogen over 2 hours. The reaction was slowly warmed up to room temperature and stirred over the week-end. After cooling into an ice-water bath, a saturated aqueous ammonium chloride solution (500 ml) was added (slowly early on) to the reaction. The phases were vigorously stirred and separated. The organic phase was washed with more ammonium chloride solution (300 ml) and brine (300 ml). Each aqueous phase was re-extracted with diethyl ether (300 ml). Combined extracts were dried over sodium sulfate. The product was purified by fractional distillation through a 20-cm Widmer column.

Provenance & Evidence