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

HRID 222461ノート

反応式

HRID 222461 の反応式
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]

参加物

4

反応物 3

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

生成物 1

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

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-e0c8d50cc63d4ad6bd10457de82110bb
出典データセット
uspto-grants-2012_06
特許番号
US08207216B2

反応ノート

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