Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → 7-Methyl-9,10-dihydroacephenanthrene

HRID 36630

Reaktionsgleichung

Reaktionsgleichung von HRID 36630
O[C:2]1([CH3:18])[CH2:16][CH2:15][CH2:14][C:13]2[C:12]3=[C:17]4[C:5]([CH2:6][CH2:7][C:8]4=[CH:9][CH:10]=[CH:11]3)=[CH:4][C:3]1=2.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:18][C:2]1[C:3]2[CH:4]=[C:5]3[C:17]4[C:8](=[CH:9][CH:10]=[CH:11][C:12]=4[C:13]=2[CH2:14][CH2:15][CH:16]=1)[CH2:7][CH2:6]3

Komponenten

5

Edukt 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 199374177-Hydroxy-7-methyl-7,8,9,10-tetrahydroacephenanthrene

Produkt 1

HCID 233640227-Methyl-9,10-dihydroacephenanthreneAusbeute 92,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 7-hydroxy-7-methyl-7,8,9,10-tetrahydroacephenanthrene (0.15 g, 0.64 mmol) and camphorsulfonic acid (0.02 g, 0.064 mmol) in toluene (20 mL) was heated at reflux for 1 h. The reaction was allowed to cool and was diluted with ethyl acetate (20 mL). The organic solution was washed with saturated aqueous sodium carbonate solution (3×15 mL) and water (3×15 mL), dried over magnesium sulfate, and concentrated under reduced pressure. The reaction product was purified by flash chromatography to give 0.13 g (92%) of the product: MS (CI) m/e (%) 221 (M+H+, 100); 1H NMR (CDCl3, 300 MHz) δ 7.69 (d, 1H, J=8.4 Hz), 7.44 (dd, 1H, J=7.0, 8.4 Hz), 7.32 (s, 1H), 7.21 (d, 1H, J=6.9 Hz), 5.94 (m, 1H), 3.38 (s, 4H), 3.09 (t, 2H, J=8.5 Hz), 2.52 (m, 2H), 2.16 (m, 3H).

Aufarbeitung

  1. temperatureat reflux for 1 h
  2. temperatureto cool
  3. washThe organic solution was washed with saturated aqueous sodium carbonate solution (3×15 mL) and water (3×15 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe reaction product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-46a158f26c644bbb9e76a987e6d0e912
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05416089

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