1-(Triphenylphosphoranylidene)acetone → 1-(5-Methoxy-1-benzofuran-3-yl)propan-2-one

HRID 1768031Notes

Reaction equation

HRID 1768031 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][CH2:9][C:8](=O)[C:7]=2[CH:12]=1.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:20][C:21](=[O:23])[CH3:22])C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][CH:9]=[C:8]([CH2:20][C:21]([CH3:22])=[O:23])[C:7]=2[CH:12]=1

Participants

4

Reactant 2

HCID 150381-(Triphenylphosphoranylidene)acetoneHCID 3466085-Methoxybenzofuran-3(2H)-one

Product 1

HCID 156187201-(5-Methoxy-1-benzofuran-3-yl)propan-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5-methoxy-benzofuran-3 (2H)-one (1.64 g, 10 mmol) and 1-triphenylphosphoranylidene-2-propanone (4.77 g, 15 mmol) was refluxed in toluene (100 ml) for 48 hrs. At the end, reaction mixture was concentrated and loaded over silica-gel column. The column was eluted with hexane (500 ml) and later with 25% ethyl acetate. The product, 1-(5-methoxy-1-benzofuran-3-yl)acetone was obtained as a red oil. Yield: 1.1 g (53%); 205 (M+H).

Workup

  1. customAt the end, reaction mixture
  2. concentrationwas concentrated
  3. washThe column was eluted with hexane (500 ml) and later with 25% ethyl acetate

Sources & evidence

ORD record
ord-98b347120454428e830ca82f0d0e0ed9
Source dataset
uspto-grants-2007_06
Patent number
US07235569B2

Reaction notes

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