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

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.

1. temperatureAfter cooling into an ice-water bath
2. customto the reaction
3. stirringThe phases were vigorously stirred
4. customseparated
5. washThe organic phase was washed with more ammonium chloride solution (300 ml) and brine (300 ml)
6. extractionEach aqueous phase was re-extracted with diethyl ether (300 ml)
7. dry with materialCombined extracts were dried over sodium sulfate
8. distillationThe product was purified by fractional distillation through a 20-cm Widmer column

ORD record

ord-e48e9c1a16254258a67de77ec9a86690

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09000226B2