Toluene → Ethyl(6-chloro-1-benzofuran-3-yl)acetate

HRID 1178794Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1178794
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=O)[CH2:7][O:8][C:4]=2[CH:3]=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:6]1[C:5]2[CH:10]=[CH:11][C:2]([Cl:1])=[CH:3][C:4]=2[O:8][CH:7]=1)[CH3:36]

Komponenten

4

Edukt 3

HCID 1140TolueneHCID 10870911Carboxymethylene triphenylphosphoraneHCID 137781336-Chloro-3-Benzofuranone

Produkt 1

HCID 12936152Ethyl(6-chloro-1-benzofuran-3-yl)acetate

Versuchsvorschrift

A mixture of 6-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. Afterwards, 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(6-chloro-1-benzofuran-3-yl)acetate, was obtained as a white oil. Yield: 2.1 g (87%); (M+H): 239.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-96aa94cd28e6428d8ce05256b1be64b4
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07276603B2

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