Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl-3-(5'-fluoro-2'-methoxyphenyl)acrylate

HRID 1919512Notes

Reaction equation

HRID 1919512 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH:7]=O.[C:12]([CH:17]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:14][CH2:15][CH3:16])=[O:13]>C(Cl)Cl>[CH2:15]([O:14][C:12](=[O:13])[CH:17]=[CH:7][C:6]1[CH:9]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[O:10][CH3:11])[CH3:16]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 27349435-Fluoro-2-methoxybenzaldehyde

Product 1

HCID 67499726Ethyl-3-(5'-fluoro-2'-methoxyphenyl)acrylateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-fluoro-2-methoxybenzaldehyde (4.3 g, 28 mmol) in dry CH2Cl2 (40 mL) at 0° C. was added carbethoxymethylenetriphenylphosphorane (10.7 g, 30 mmol) portionwise and the reaction was warmed to room temperature for 12 h. The solvent was then removed in vacuo and the residue was purified by flash column chromatography (8% EtOAc in Hexane, Rf=0.20) to yield the product (4 g, 95%) as an oil.

Workup

  1. customThe solvent was then removed in vacuo
  2. customthe residue was purified by flash column chromatography (8% EtOAc in Hexane, Rf=0.20)

Sources & evidence

ORD record
ord-2d7fad6a9b744decb359b7b4e6c0050e
Source dataset
uspto-grants-2012_05
Patent number
US08168635B2

Reaction notes

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