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

HRID 1178802Notes

Reaction equation

HRID 1178802 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 then 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%); (M+H): 239.

Workup

  1. customAt the end, reaction mixture
  2. concentrationwas concentrated
  3. washThe column was eluted with hexane (500 ml)

Sources & evidence

ORD record
ord-68b5ecaceec34b588afcd4f9526fae38
Source dataset
uspto-grants-2007_10
Patent number
US07276603B2

Reaction notes

Loading…