Tin tetrachloride → 1-[2-(6-Methoxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone

HRID 1359191ノート

反応式

HRID 1359191 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[O:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[CH:17]=1)[CH:7]=[CH:6]2.[C:22](Cl)(=[O:27])[CH2:23][CH2:24][CH2:25][CH3:26].[Sn](Cl)(Cl)(Cl)Cl>C(Cl)(Cl)Cl.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[O:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[C:17]=1[C:22](=[O:27])[CH2:23][CH2:24][CH2:25][CH3:26])[CH:7]=[CH:6]2

参加物

6

反応物 3

HCID 24287Tin tetrachlorideHCID 61186Valeryl chlorideHCID 110766242-(6-Methoxy-2-naphthyl)-1-benzofuran

生成物 1

HCID 113372811-[2-(6-Methoxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone収率 60.2%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-20 °C

実験手順

To a stirring mixture of 2-(6-methoxy-2-naphthyl)-1-benzofuran (4.02 g, 14.7 mmol) in chloroform (70 mL) chilled in an ice bath was added valeryl chloride (2.6 mL, 22 mmol). The reaction mixture was chilled to −20° C. and tin (IV) chloride (2.2 mL, 19 mmol) was added, dropwise. The mixture was then stirred at room temperature for one hour and then refluxed for 3 hours, 20 minutes. It was allowed to cool to room temperature and poured into ice. The organic phase was diluted with excess ethyl acetate and washed with water and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and solvent evaporated. The residue was purified twice by flash chromatography (Biotage apparatus) using 2% ethyl acetate in hexane and 10-50% chloroform in hexane to afford 1-[2-(6-methoxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone as a yellow gum (3.17 g). Mass spectrum (+EI, M+) m/z358. 1HNMR (400 MHz, DMSO-d6): δ8.35 (s, 1H), 8.0-8.05 (m, 3H), 7.8 (dd, 1H, J=8.5 Hz and 1.7 Hz), 7.7-7.75 (m, 1H), 7.4-7.45 (m, 3H), 7.25-7.3 (m, 1H), 3.9 (s, 3H), 2.7 (t, 2H, J=7.3 Hz), 1.5-1.6 (m, 2H), 1.1-1.2 (m, 2H), and 0.7 ppm (t, 3H, J=7.4 Hz).

後処理

  1. temperaturechilled in an ice bath
  2. temperaturerefluxed for 3 hours, 20 minutes
  3. temperatureto cool to room temperature
  4. additionpoured into ice
  5. washwashed with water and brine
  6. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customsolvent evaporated
  9. customThe residue was purified twice by flash chromatography (Biotage apparatus)

出典と根拠

ORDレコード
ord-59568442c3bd45adbdd03930d3274404
出典データセット
uspto-grants-2003_07
特許番号
US06599925B2

反応ノート

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