Triphenylmethyl phosphonium bromide → 1-[5-(Trifluoromethyl)-2-vinylphenyl]prop-2-en-1-ol

Temperature

0 °C

Triphenylmethylphosphonium bromide (1.71 g, 4.78 mmol) was dissolved in ether (20.00 mL). After cooling to 0° C., a 1.60 M solution of n-butyllithium in hexane (2.72 mL) was added rapidly by syringe and the resulting orange mixture was warmed to room temperature and stirred overnight. The stirring was stopped to allow the solids to settle and then the ylid was transferred via cannula to a solution of 5-(trifluoromethyl)-3-vinyl-1,3-dihydro-2-benzofuran-1-ol (1.00 g, 4.34 mmol) in ether (10.00 mL) while stirring at 0° C. Following the addition, the ice bath was removed and the mixture was heated to reflux overnight. The reaction was allowed to cool and then the solids filtered off and washed with a small amount of ether. Most of the solvents were evaporated and the crude product was loaded onto silica gel and eluted with hexane/EtOAc (10:1) to give the desired product (0.81 g, 82%), LC-MS [M+1]=229.2.

1. temperaturethe resulting orange mixture was warmed to room temperature
2. stirringwhile stirring at 0° C
3. additionthe addition
4. customthe ice bath was removed
5. temperaturethe mixture was heated
6. temperatureto reflux overnight
7. temperatureto cool
8. filtrationthe solids filtered off
9. washwashed with a small amount of ether
10. customMost of the solvents were evaporated
11. washeluted with hexane/EtOAc (10:1)

ORD record

ord-34268934a841466189f6b29463e208fb

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680104B2