Methyl (E)-3-fluorocinnamate → (2E)-3-(3-fluorophenyl)prop-2-en-1-ol

Temperature

-30 °C

To a solution of trans-3-fluorocinnamic acid methyl ester (69.61 g, 386 mmol) in dry dichloromethane (1 L) at −78° C. under nitrogen was added dropwise diisobutylaluminum hydride (neat, 172 mL, 965 mmol, 2.5 equiv.) via an addition funnel. After the addition was complete, the reaction mixture was allowed to warm to −30° C. and stirred for an additional 1 hour, then quenched with methanol (150 mL). Upon warming to room temperature, the reaction mixture was treated with saturated aqueous solution of sodium/potassium tartrate (300 mL) and stirred for 30 minutes. The organic layer was washed sequentially with 1 N aqueous hydrochloric acid solution, saturated aqueous sodium bicarbonate solution, brine, and dried (anhydrous sodium sulfate). The crude oil was purified by silica gel chromatography (0-50% ethyl acetate:hexane) to give 53.07 g (90%) of trans-3-fluorocinnamyl alcohol as a colorless oil. MS (ES) m/z 152.1 (M+).

1. additionAfter the addition
2. customquenched with methanol (150 mL)
3. temperatureUpon warming to room temperature
4. additionthe reaction mixture was treated with saturated aqueous solution of sodium/potassium tartrate (300 mL)
5. stirringstirred for 30 minutes
6. washThe organic layer was washed sequentially with 1 N aqueous hydrochloric acid solution, saturated aqueous sodium bicarbonate solution, brine
7. dry with materialdried (anhydrous sodium sulfate)
8. customThe crude oil was purified by silica gel chromatography (0-50% ethyl acetate:hexane)

ORD record

ord-71fd992ebfa045c980d9973d3730aff2

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07517899B2