Toluene → Ethyl(6-chloro-1-benzofuran-3-yl)acetate

HRID 1767992Notes

Reaction equation

HRID 1767992 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=O)[CH2:7][O:8][C:4]=2[CH:3]=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:6]1[C:5]2[CH:10]=[CH:11][C:2]([Cl:1])=[CH:3][C:4]=2[O:8][CH:7]=1)[CH3:36]

Participants

4

Reactant 3

HCID 1140TolueneHCID 10870911Carboxymethylene triphenylphosphoraneHCID 137781336-Chloro-3-Benzofuranone

Product 1

HCID 12936152Ethyl(6-chloro-1-benzofuran-3-yl)acetate

Procedure

A mixture of 6-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, the reaction mixture was concentrated and loaded over a silica-gel column. The column was eluted with hexane (500 ml) and later with 25% ethyl acetate. The product, ethyl(6-chloro-1-benzofuran-3-yl)acetate, was obtained as a white oil. Yield: 2.1 g (87%); 239 (M+H).

Workup

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

Sources & evidence

ORD record
ord-610e968e9bc84b3694fa106934be9194
Source dataset
uspto-grants-2007_06
Patent number
US07235569B2

Reaction notes

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