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

HRID 222461

Reaction equation

HRID 222461 reaction equation
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]

Participants

4

Reactant 3

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

Product 1

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

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-e0c8d50cc63d4ad6bd10457de82110bb
Source dataset
uspto-grants-2012_06
Patent number
US08207216B2

Linked notes

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