Toluene → Ethyl 2-(benzofuran-3-yl)acetate

HRID 1767989

Reaction equation

HRID 1767989 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3](=O)[CH2:2]1.[C:11]([CH:14]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:13])=[O:12].[C:34]1(C)C=CC=C[CH:35]=1>>[CH2:34]([O:13][C:11](=[O:12])[CH2:14][C:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:1][CH:2]=1)[CH3:35]

Participants

4

Reactant 3

HCID 1140TolueneHCID 23556CoumaranoneHCID 10870911Carboxymethylene triphenylphosphorane

Product 1

HCID 7537531Ethyl 2-(benzofuran-3-yl)acetate

Procedure

A mixture of benzofuran-3 (2H)-one (1.34 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(-1-benzofuran-3-yl)acetate, was obtained as a white oil. Yield: 2.0 g (98%); 205 (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-78dd9984ac1340d183623bb21ead034b
Source dataset
uspto-grants-2007_06
Patent number
US07235569B2

Linked notes

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