Toluene → Ethyl(7-methoxy-1-benzofuran-3-yl)acetate

HRID 1768004

Reaction equation

HRID 1768004 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[O:10][CH2:9][C:8](=O)[C:7]=2[CH:6]=[CH:5][CH:4]=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:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:11]=2[O:10][CH:9]=1)[CH3:37]

Participants

4

Reactant 3

HCID 1140TolueneHCID 28181127-Methoxybenzofuran-3(2H)-oneHCID 10870911Carboxymethylene triphenylphosphorane

Product 1

HCID 22734085Ethyl(7-methoxy-1-benzofuran-3-yl)acetate

Procedure

A mixture of 7-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(7-methoxy-1-benzofuran-3-yl)acetate was obtained as a white oil. Yield: 1.9 g (81%); 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-271ad550a4094ff1868339aa7e1105cd
Source dataset
uspto-grants-2007_06
Patent number
US07235569B2

Linked notes

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