Toluene → (6-Acetoxymethyl-benzofuran-3-yl)-acetic acid ethyl ester

HRID 222461

Reaktionsgleichung

Reaktionsgleichung von HRID 222461
O=[C:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][O:12][C:13](=[O:15])[CH3:14])=[CH:10][C:5]=2[O:4][CH2:3]1.[C:16]([CH:19]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:18])=[O:17].[C:39]1(C)C=CC=C[CH:40]=1>>[CH2:39]([O:18][C:16](=[O:17])[CH2:19][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][O:12][C:13](=[O:15])[CH3:14])=[CH:10][C:5]=2[O:4][CH:3]=1)[CH3:40]

Komponenten

4

Edukt 3

HCID 1140TolueneHCID 10870911Carboxymethylene triphenylphosphoraneHCID 68526065Acetic acid 3-oxo-2,3-dihydro-benzofuran-6-ylmethyl ester

Produkt 1

HCID 68523733(6-Acetoxymethyl-benzofuran-3-yl)-acetic acid ethyl ester

Versuchsvorschrift

To a solution of acetic acid 3-oxo-2,3-dihydro-benzofuran-6-ylmethyl ester (1.50 g, 7.27 mmol) in toluene (260 mL) was added (caboxymethylene)triphenyl phosphorane (12.67 g, 36.37 mmol) and the mixture was refluxed for 24 h. The reaction mixture was allowed to cool to room temperature and concentrated. The residue was purified by column chromatography (ethylacetate:hexane; 5:95) to give the (6-acetoxymethyl-benzofuran-3-yl)-acetic acid ethyl ester as a off white solid (1.15 g, 57%). 1H NMR (CDCl3, 400 MHz) 1.27 (t, J=7.1 Hz, 3H), 2.11 (s, 3H), 3.69 (s, 2H), 4.19 (q, J=7.1 Hz, 2H), 5.21 (s, 2H), 7.26 (d, J=8.0 Hz, 1H), 7.50 (s, 1H), 7.56 (d, J=8.0 Hz, 1H), 7.65 (s, 1H), 13C NMR (CDCl3, 100 MHz) 14.2, 21.0, 29.9, 61.1, 66.4, 111.6, 113.1, 119.8, 123.1, 127.7, 132.6, 143.5, 155.2, 170.5, 170.9.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 24 h
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography (ethylacetate:hexane; 5:95)

Quellen und Nachweise

ORD-Eintrag
ord-e0c8d50cc63d4ad6bd10457de82110bb
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207216B2

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