Hydroquinone → 4a,5,8,8a-Tetrahydro-2,8-dimethoxy-6-trimethylsilyloxynapthalene-1,4-dione

HRID 726193Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 726193
[CH3:1][O:2][C:3]1[C:4](=[O:10])[CH:5]=[CH:6][C:7](=[O:9])[CH:8]=1.C1(C=CC(O)=CC=1)O.[CH3:19][O:20][CH:21]=[CH:22][C:23]([O:25][Si:26]([CH3:29])([CH3:28])[CH3:27])=[CH2:24]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4](=[O:10])[CH:5]2[CH:6]([C:7](=[O:9])[CH:8]=1)[CH2:24][C:23]([O:25][Si:26]([CH3:27])([CH3:29])[CH3:28])=[CH:22][CH:21]2[O:20][CH3:19]

Komponenten

5

Edukt 3

HCID 785HydroquinoneHCID 761462-Methoxy-1,4-benzoquinoneHCID 1010511-Methoxy-3-trimethylsilyloxy-1,3-butadiene

Produkt 1

HCID 197105404a,5,8,8a-Tetrahydro-2,8-dimethoxy-6-trimethylsilyloxynapthalene-1,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

In a 50 mL round bottom flask, 2-methoxy-1,4-benzoquinone (2.3 g, 16.7 mmol) was suspended in toluene (30 mL). Hydroquinone (95 mg) was added and the resulting suspension was stirred magnetically for 5 min. 1-Methoxy-3-trimethylsilyloxy-1,3-butadiene (Aldrich, used as received, 5.0 g, 4.5 mL, 29.1 mmol) was added in one portion and the reaction was heated under N2 at 60° C. using an oil bath for 18 h. The reaction was removed from the oil bath, allowed to cool to rt and the solvent was removed by evaporation. Crystallization occurred after cooling the mixture to -30° C. for 1 hour. The colorless solid was collected by filtration and washed with hexane (30 mL) giving 4a,5,8,8a-tetrahydro-2,8-dimethoxy-6-trimethylsilyloxynapthalene-1,4-dione ##STR137## as a colorless powder (3.6 g, 11.6 mmol, 70%, >95% pure by 1H NMR, mp 108°-110° C.; 1H NMR (CDCl3) δ0.52 (s, 9H), 2.2-2.4 (m, 2H), 3.18 (s, 3H), 3.47 (t, 1H), 3.80 (s, 3H), 3.92 (m, 2H), 5.20 (d, 1H), 6.12 (s, 1H).

Aufarbeitung

  1. customfor 18 h
  2. customThe reaction was removed from the oil bath
  3. temperatureto cool to rt
  4. customthe solvent was removed by evaporation
  5. customCrystallization
  6. temperatureafter cooling the mixture to -30° C. for 1 hour
  7. filtrationThe colorless solid was collected by filtration
  8. washwashed with hexane (30 mL)

Quellen und Nachweise

ORD-Eintrag
ord-7a32baf5814e4b44b6d1f0e7eb3185b1
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05708168

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