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

HRID 222461

반응식

HRID 222461 반응식
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]

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-e0c8d50cc63d4ad6bd10457de82110bb
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207216B2

연결된 노트

불러오는 중…