Water → Ethyl 3-(4-fluorophenyl)acrylate

4-Fluorobenzaldehyde (9.61 g, 80.0 mmol) in tetrahydrofuran (120 mL) was mixed with ethyl 2-(diethoxyphosphoryl)acetate (17.9 g, 80.0 mmol) under cooling with ice, and then sodium ethoxide-ethanol solution (21 wt %, 44.8 mL, 120 mmol) was added dropwise to the reaction mixture under cooling with ice, and the resulting reaction mixture was stirred at room temperature for 2 hours. After addition of water, the reaction mixture was extracted with ethyl acetate, and the organic layer dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1→10/1 (v/v)) to give the title compound as a colorless oil (14.1 g, yield 91%).

1. temperatureunder cooling with ice
2. temperatureunder cooling with ice
3. customthe resulting reaction mixture
4. extractionthe reaction mixture was extracted with ethyl acetate
5. dry with materialthe organic layer dried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1→10/1 (v/v))

ORD record

ord-a09054b200b64d068416ddf3a74431a4

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09216999B2