3-Methoxyacetophenone → HCID 68877312, compound

HRID 1436006Notes

Reaction equation

HRID 1436006 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9](=O)[CH3:10])[CH:6]=[CH:7][CH:8]=1.[CH3:12][O:13][C:14](=[O:35])[CH:15]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:12][O:13][C:14](=[O:35])[CH:15]=[C:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:10]

Participants

4

Reactant 2

HCID 114603-MethoxyacetophenoneHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester

Product 1

HCID 68877312HCID 68877312, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-(3-Methoxyphenyl)ethanone (15 g, 0.1 mmol) and methyl(triphenylphosphoranylidene)acetate (62 g, 0.186 mmol) in toluene (75 ml) were heated at 100° C. for 2 days. After allowing cooling to ambient temperature the solvent was removed under reduced pressure to give crude product. Precipitation with EtOAc and heptane followed by flash chromatography of the concentrated mother liquor on silica (eluent: 20% EtOAc in heptane) afforded the product as a mixture of geometric isomers (21.8 g, 86%).

Workup

  1. customwas removed under reduced pressure
  2. customto give crude product
  3. customPrecipitation with EtOAc and heptane
  4. customafforded the product
  5. additionas a mixture of geometric isomers (21.8 g, 86%)

Sources & evidence

ORD record
ord-6a9f6016e9c94f21a9d49204a17fc54d
Source dataset
uspto-grants-2009_11
Patent number
US07618985B2

Reaction notes

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