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

HRID 1768008Notes

Reaction equation

HRID 1768008 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.[C:13]([CH:16]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:15])=[O:14].[C:36]1(C)C=CC=C[CH:37]=1>>[CH2:36]([O:15][C:13](=[O:14])[CH2:16][C:8]1[C:7]2[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=2[O:10][CH:9]=1)[CH3:37]

Participants

4

Reactant 3

HCID 1140TolueneHCID 3466085-Methoxybenzofuran-3(2H)-oneHCID 10870911Carboxymethylene triphenylphosphorane

Product 1

HCID 15618718Ethyl(5-methoxy-1-benzofuran-3-yl)acetate

Procedure

A mixture of 5-methoxy-benzofuran-3 (2H)-one (1.64 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 silica-gel column. The column was eluted with hexane (500 ml) and later with 25% ethyl acetate. The product, ethyl(5-methoxy-1-benzofuran-3-yl)acetate, was obtained as a white oil. Yield: 1.6 g (68%); 235 (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-f10756087f0841ed80c5a5bc3b4408c2
Source dataset
uspto-grants-2007_06
Patent number
US07235569B2

Reaction notes

Loading…