Ethyl Acetate → (E)-3-(4-bromophenyl)-3-(4-trifluoromethylphenyl)-prop-2-en-1-ol

Temperature

0 °C

Sodium methoxide (23 mg, 0.43 mmol) was added to 1M solution of lithium aluminum hydride in tetrahydrofuran (9 mL, 9.0 mmol). The mixture was cooled to 0° C. and a solution of 3-(4-bromophenyl)prop-2-yn-1-ol (1.9 g, 9.0 mmol) in tetrahydrofuran (15 mL) was slowly added. The reaction was stirred for at 0° C. for 3 h; ethyl acetate (2.7 mL, 9.0 mmol) was added and the mixture was stirred for 10 min without cooling. 4-Iodobenzotrifluoride (2.33 g, 8.6 mmol), anhydrous zinc chloride (0.74 g, 5.4 mmol), tris(dibenzylideneacetone)dipalladium chloroform complex (0.19 g, 0.18 mmol) and tri(2-furyl)phosphine (0.17 g, 0.73 mmol) were added, the mixture was evacuated and kept under nitrogen. The mixture was heated at 65° C. for 16 h. Methanol (4.5 mL) was added and the mixture was stirred for additional 1 h. The reaction mixture was diluted with ether (300 mL) and saturated aqueous solution of ammonium chloride (2.5 mL) was added. The mixture was filtered through a pad of silica gel, evaporated in vacuo and the residue was submitted to column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 80:20) affording (E)-3-(4-bromophenyl)-3-(4-trifluoromethylphenyl)-prop-2-en-1-ol.

1. stirringthe mixture was stirred for 10 min
2. temperaturewithout cooling
3. customthe mixture was evacuated
4. temperatureThe mixture was heated at 65° C. for 16 h
5. additionMethanol (4.5 mL) was added
6. stirringthe mixture was stirred for additional 1 h
7. additionThe reaction mixture was diluted with ether (300 mL) and saturated aqueous solution of ammonium chloride (2.5 mL)
8. additionwas added
9. filtrationThe mixture was filtered through a pad of silica gel
10. customevaporated in vacuo

ORD record

ord-777d2d51e5cf476ba870c0d0d6da8bd5

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08551993B2