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

HRID 1178791Notes

Reaction equation

HRID 1178791 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, the reaction mixture was concentrated and loaded over a silica-gel column. The column was eluted with hexane (500 ml) and then with 25% ethyl acetate. The product, ethyl(-1-benzofuran-3-yl)acetate was obtained as a white oil. Yield: 2.0 g (98%); (M+H): 205.

Workup

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

Sources & evidence

ORD record
ord-09c5d5cb2e7f4ff48cf7c76821320af1
Source dataset
uspto-grants-2007_10
Patent number
US07276603B2

Reaction notes

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