2-Propenoic acid, 3-[4-(trifluoromethyl)phenyl]-, ethyl ester → (E)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-ol

(E)-Ethyl 3-(4-(trifluoromethyl)phenyl)acrylate (25.00 g, 102 mmol) in 100 mL ether was cooled in an ice-water bath. To this solution, di-iso-butylaluminum hydride (205 mL, 205 mmol) in hexane was added. After addition, the ice-water bath was removed. After 2 hours of stirring at room temperature, the reaction mixture was diluted with 200 mL diethyl ether, cooled to 0° C. and quenched with careful addition of 200 mL brine and 200 mL of 5.0 M HCl. The aqueous solution was extracted with diethyl ether twice (200 mL each time). The combined organic phases were washed with brine and dried over sodium sulfate. The product was chromatographed eluting with 20% EtOAc in hexane. After removing the solvent, a white solid was obtained as the desired product (15.3 g, yield=74%). 1H NMR (400 MHz, CD3OD) δ ppm 4.28 (dd, J=5.28, 1.57 Hz, 2H) 6.55 (dt, J=15.94, 5.23 Hz, 1H) 6.67-6.75 (m, 1H) 7.58-7.67 (m, 4H).

1. additionAfter addition
2. customthe ice-water bath was removed
3. additionthe reaction mixture was diluted with 200 mL diethyl ether
4. temperaturecooled to 0° C.
5. customquenched with careful addition of 200 mL brine and 200 mL of 5.0 M HCl
6. extractionThe aqueous solution was extracted with diethyl ether twice (200 mL each time)
7. washThe combined organic phases were washed with brine
8. dry with materialdried over sodium sulfate
9. customThe product was chromatographed
10. washeluting with 20% EtOAc in hexane
11. customAfter removing the solvent

ORD record

ord-a73c01f3601746a2a7fc57462ef66946

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08084479B2