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

HRID 1359191Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1359191
[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

Komponenten

6

Edukt 3

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

Produkt 1

HCID 113372811-[2-(6-Methoxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanoneAusbeute 60,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-59568442c3bd45adbdd03930d3274404
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06599925B2

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