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

HRID 222458

Reaktionsgleichung

Reaktionsgleichung von HRID 222458
[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]

Komponenten

4

Edukt 3

HCID 1140TolueneHCID 23556CoumaranoneHCID 10870911Carboxymethylene triphenylphosphorane

Produkt 1

HCID 7537531Ethyl 2-(benzofuran-3-yl)acetateAusbeute 58 %

Versuchsvorschrift

To a solution of benzofuran-3-one (1.00 g, 7.45 mmol) in toluene (25 mL) was added (carboxymethylene)triphenyl phosphorane (3.92 g, 11.2 mmol), and the mixture was refluxed for 24 h. The reaction mixture was cooled to room temperature and concentrated. The residue was purified by column chromatography (hexane, then ethyl acetate:hexane; 1:3) to give a product (0.89 g, 58%). The spectral data for this compound are identical to that reported in the literature. (Deshpande, A. R.; Paradkar, M. V. Syn.Commun., 1990, 20, 809).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 24 h
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography (hexane

Quellen und Nachweise

ORD-Eintrag
ord-1513cc8125f34864afdb3594f4dce104
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207216B2

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