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

HRID 250844Notes

Reaction equation

HRID 250844 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 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

5.0 g (14.95 mmol, 1.5 eq) of methyl (triphenylphosphoranylidene)acetate are added to a solution of 3.25 g (9.6 mmol, 1 eq) of 3-benzyloxy-4-iodobenzaldehyde in 15 ml of toluene. The reaction mixture is heated at 90° C. for 1 hour. The solvent is evaporated off and the oil obtained is chromatographed on silica gel (8/2 heptane/ethyl acetate). After recrystallization from dichloromethane/heptane, 2.59 g of methyl (E)-3-(3-benzyloxy-4-iodophenyl)acrylate are obtained. Yield=68%

Workup

  1. customThe solvent is evaporated off
  2. customthe oil obtained
  3. customis chromatographed on silica gel (8/2 heptane/ethyl acetate)
  4. customAfter recrystallization from dichloromethane/heptane, 2.59 g of methyl (E)-3-(3-benzyloxy-4-iodophenyl)acrylate
  5. customare obtained

Sources & evidence

ORD record
ord-cb76c9a0573042d9944546511020a2aa
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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