7-Methyl-9,10-dihydroacephenanthrene → 7-Methylacephenanthrylene

HRID 36631

Reaktionsgleichung

Reaktionsgleichung von HRID 36631
[CH3:1][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>O1CCOCC1.C(OCC)(=O)C.O>[CH3:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:3]=1[CH:4]=[C:5]1[C:17]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]2=3)[CH:7]=[CH:6]1

Komponenten

5

Edukt 1

HCID 233640227-Methyl-9,10-dihydroacephenanthrene

Produkt 1

HCID 149320397-MethylacephenanthryleneAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 7-methyl-9,10-dihydroacephenanthrene (0.13 g, 0.59 mmol) and dichlorodicyanoquinone (0.27 g, 1.18 mmol) in dioxane (10 ml) was heated at reflux for 0.5 h. The reaction mixture was allowed to cool and was diluted with ethyl acetate (50 mL) and water (20 mL). The organic layer was separated, washed with water (3×20 mL) and brine solution (3×20 mL), dried (MgSO4), and concentrated under reduced pressure. The resulting solid was purified by flash chromatography to give 0.07 g (57%) of the product: 1H NMR (CDCl3, 300 MHz) δ 8.54 (d, 1H, J=8.0 Hz), 8.40 (dd, 1H, J=7.3, 6.9 Hz), 8.24 (s, 1H), 7.66 (m, 2H), 7.58 (dd, 1H, J=8.4, 7.3 Hz), 7.46 (d, 1H, J=7.3 Hz), 7.20 (d, 1H, J= 5.1 Hz), 7.16 (d, 1H, J=5.4 Hz), 2.82 (s, 3H).

Aufarbeitung

  1. temperatureat reflux for 0.5 h
  2. temperatureto cool
  3. customThe organic layer was separated
  4. washwashed with water (3×20 mL) and brine solution (3×20 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting solid was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bce723b98280443fb7ed47abb8f261cf
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05416089

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