4-Fluorobenzaldehyde → (E)-ethyl 3-(4-fluorophenyl)-2-methylacrylate

HRID 514655Notes

Reaction equation

HRID 514655 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([CH2:15][CH:16]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:12][CH2:13][CH3:14])=[O:11]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[C:15](\[CH3:16])/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 680234-FluorobenzaldehydeHCID 12607919Ethyl 3-(triphenyl-lambda~5~-phosphanylidene)propanoate

Product 1

HCID 12016768(E)-ethyl 3-(4-fluorophenyl)-2-methylacrylateYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Fluorobenzaldehyde (12 g, 97 mmol) was dissolved in toluene (500 mL). (Carboethoxyethylidene)triphenylphosphorane (42 g, 116 mmol) was added and the mixture was heated to reflux until the starting material was consumed. The solution was cooled, diluted with hexanes, and the solid was filtered. The filtrate was evaporated in vacuo. The remaining residue was dissolved in ether, and filtered through a plug of silica gel using ether as eluent. The solvents were evaporated in vacuo to afford the title compound (20 g, 99% yield) as a yellow solid. 1H NMR (DMSO-d6) δ ppm: 7.64 (s, 1H), 7.38 (dd, J=8.65, 5.59 Hz, 2H), 7.08 (t, J=8.65 Hz, 2H), 4.27 (q, J=7.12 Hz, 2H), 2.10 (d, J=1.36 Hz, 3H), 1.27-1.38 (m, 3H). MS (DCI+) 209 (M+H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux until the starting material
  3. customwas consumed
  4. temperatureThe solution was cooled
  5. additiondiluted with hexanes
  6. filtrationthe solid was filtered
  7. customThe filtrate was evaporated in vacuo
  8. dissolutionThe remaining residue was dissolved in ether
  9. filtrationfiltered through a plug of silica gel
  10. customThe solvents were evaporated in vacuo

Sources & evidence

ORD record
ord-127f0236aefb4b079c8d76169d4c4d29
Source dataset
uspto-grants-2015_08
Patent number
US09108905B2

Reaction notes

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