4-Fluorobenzaldehyde → Ethyl 3-(4-fluorophenyl)prop-2-enoate

HRID 1592361Notes

Reaction equation

HRID 1592361 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([CH:15]=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>[CH2:13]([O:12][C:10](=[O:11])[CH:15]=[CH:6][C:5]1[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=1)[CH3:14]

Participants

4

Reactant 2

HCID 680234-FluorobenzaldehydeHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester

Product 1

HCID 367200Ethyl 3-(4-fluorophenyl)prop-2-enoateYield 99.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Fluorobenzaldehyde (27.2 ml, 0.23 Mol) and carboethoxymethylenetriphenylphosphorane (88.38 g, 0.23 Mol) were disolved in toluene (500 ml), and the mixture was heated overnight at reflux. The reaction was stripped then purified by flash chromatography in 25% EtOAc/Hexanes yielded 44.55g of a crystalline solid as product. NMR (300 MHz, CDCl3) δ 7.65 (d, 1H, J=16 Hz); 7.60-7.40 (m, 2H); 7.08 (t, 2H, J=7 Hz); 6.35 (d, 1H, J=16 Hz); 4.26 (q, 2H, J=7 Hz); 1.34 (t, 3H, J=7 Hz).

Workup

  1. temperaturethe mixture was heated overnight
  2. temperatureat reflux
  3. customThe reaction was stripped then purified by flash chromatography in 25% EtOAc/Hexanes

Sources & evidence

ORD record
ord-4025d924ae264fbda7a9c6fcc2fca1a8
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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