Sodium Acetate → Acetic acid 3-oxo-2,3-dihydro-benzofuran-6-ylmethyl ester

HRID 222460노트

반응식

HRID 222460 반응식
Cl[CH2:2][C:3]([C:5]1[CH:15]=[CH:14][C:8]([CH2:9][O:10][C:11](=[O:13])[CH3:12])=[CH:7][C:6]=1[OH:16])=[O:4].C([O-])(=O)C.[Na+]>CO>[O:4]=[C:3]1[C:5]2[CH:15]=[CH:14][C:8]([CH2:9][O:10][C:11](=[O:13])[CH3:12])=[CH:7][C:6]=2[O:16][CH2:2]1

참가 물질

4

반응물 2

HCID 517045Sodium AcetateHCID 86637759Acetic acid 4-(2-chloro-acetyl)-3-hydroxy-benzyl ester

생성물 1

HCID 68526065Acetic acid 3-oxo-2,3-dihydro-benzofuran-6-ylmethyl ester

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of acetic acid 4-(2-chloro-acetyl)-3-hydroxy-benzyl ester (2.20 g, 9.07 mmol) and sodium acetate (1.49 g, 18.13 mmol) in anhydrous methanol (40 mL) was heated to reflux for 2 h. The reaction mixture was allowed to cool to RT, and concentrated. The residue was dissolved in dichloromethane and washed with water. The aqueous phase was extracted with dichloromethane. The combined organic layers were dried over Na2SO4, evaporated in vacuo, and the residue was purified by column chromatography (ethylacetate:hexane; 2:8) to give the acetic acid 3-oxo-2,3-dihydro-benzofuran-6-ylmethyl ester as an off white solid (1.29 g, 59%). 1H NMR (CDCl3, 400 MHz) 2.17 (s, 3H), 4.65 (s, 2H), 5.17 (s, 2H), 7.06 (d, J=8.0 Hz, 1H), 7.13 (s, 1H), 7.67 (d, J=8.0 Hz, 1H), 11.67 (s, 1H), 13C NMR (CDCl3, 100 MHz) 20.8, 65.3, 75.1, 112.3, 120.8, 121.2, 124.2, 146.9, 170.5, 174.2, 199.2.

후처리

  1. temperatureto reflux for 2 h
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with water
  5. extractionThe aqueous phase was extracted with dichloromethane
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. customevaporated in vacuo
  8. customthe residue was purified by column chromatography (ethylacetate:hexane; 2:8)

출처 및 근거

ORD 기록
ord-2e863467ecc04178a1b36d8d8f94c04a
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207216B2

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