Toluene → Ethyl(5-chloro-1-benzofuran-3-yl)acetate

HRID 1768033Notes

Reaction equation

HRID 1768033 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][C:7](=O)[C:6]=2[CH:11]=1.[C:12]([CH:15]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:14])=[O:13].[C:35]1(C)C=CC=C[CH:36]=1>>[CH2:35]([O:14][C:12](=[O:13])[CH2:15][C:7]1[C:6]2[CH:11]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:9][CH:8]=1)[CH3:36]

Participants

4

Reactant 3

HCID 1140TolueneHCID 37113525-Chloro-2,3-dihydro-1-benzofuran-3-oneHCID 10870911Carboxymethylene triphenylphosphorane

Product 1

HCID 12936153Ethyl(5-chloro-1-benzofuran-3-yl)acetate

Procedure

A mixture of 5-chloro-benzofuran-3 (2H)-one (1.68 g, 10 mmol) and (carboxymethylene)triphenylphosphorane (5.22 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, ethyl(5-chloro-1-benzofuran-3-yl)acetate was obtained as a white oil. Yield: 1.8 g (75%); 239 (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-42154745252f452aaaaf50e4358390a2
Source dataset
uspto-grants-2007_06
Patent number
US07235569B2

Reaction notes

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