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

HRID 250870Notes

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

Conditions

Temperature: 90 °C

Procedure

5.0 g (14.95 mmol, 1.8 eq) of methyl triphenylphosphoranylideneacetate are added to a solution of 3.25 g (8.2 mmol, 1 eq) of 3-benzyloxy-4-iodobenzaldehyde in 15 ml of toluene. The reaction mixture is stirred for 1 hour at 90° C. The solvent is evaporated off and the residual oil is then chromatographed on silica gel (8/2 heptane/ethyl acetate) and recrystallized from dichloromethane/heptane. 2.59 g of methyl (E)-3-(3-benzyloxy-4-iodophenyl)acrylate are obtained in solid form. Yield=68%

Workup

customThe solvent is evaporated off
customthe residual oil is then chromatographed on silica gel (8/2 heptane/ethyl acetate)
customrecrystallized from dichloromethane/heptane

Sources & evidence

ORD record: ord-2c50acde25fd4855bc4ee140fd2ff907
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863332B2

Reaction notes

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