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

HRID 1767998Notes

Reaction equation

HRID 1767998 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 a 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-2aaccd3a2d09422f82c582d31508503a
Source dataset
uspto-grants-2007_06
Patent number
US07235569B2

Reaction notes

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