Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → methyl(E)-3-(3-benzyloxy-4-iodophenyl)acrylate

HRID 1361082Notes

Reaction equation

HRID 1361082 reaction equation
C1(P(=[CH:20][C:21]([O:23][CH3:24])=[O:22])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:25]([O:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][C:40]=1[I:41])[CH:36]=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1(C)C=CC=CC=1>[CH2:25]([O:32][C:33]1[CH:34]=[C:35](/[CH:36]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])[CH:38]=[CH:39][C:40]=1[I:41])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 534172453-(Benzyloxy)-4-iodobenzaldehyde

Product 1

HCID 66971542methyl(E)-3-(3-benzyloxy-4-iodophenyl)acrylateYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

170 g (506 mmol) of methyl (triphenylphosphoranylidene)acetate are added to a solution of 114 g (337 mmol) of 3-benzyloxy-4-iodobenzaldehyde in 570 ml of toluene. The reaction mixture is refluxed for 2 hours. The solvent is evaporated off and the oil obtained is purified by chromatography on a column of silica eluted with a 50/50 heptane/dichloromethane mixture. 115 g (87%) of methyl(E)-3-(3-benzyloxy-4-iodophenyl)acrylate are obtained in the form of pale yellow crystals.

Workup

  1. temperatureThe reaction mixture is refluxed for 2 hours
  2. customThe solvent is evaporated off
  3. customthe oil obtained
  4. customis purified by chromatography on a column of silica
  5. washeluted with a 50/50 heptane/dichloromethane mixture

Sources & evidence

ORD record
ord-7c5cd54ad8804c208967e63fc456a04e
Source dataset
uspto-grants-2011_02
Patent number
US07879907B2

Reaction notes

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