Hydrochloric Acid → (3RS,4SR)-3-(3,4-dimethoxyphenyl)-4-nitrocyclohexanone

HRID 73495

Reaktionsgleichung

Reaktionsgleichung von HRID 73495
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[N+:11]([O-:13])=[O:12])=[CH:5][C:4]=1[O:14][CH3:15].C[Si](C)(C)[O:18][C:19]([CH:21]=[CH2:22])=[CH2:20].C1(C)C=CC=CC=1.Cl>C(OCC)(=O)C>[CH3:15][O:14][C:4]1[CH:5]=[C:6]([CH:9]2[CH:10]([N+:11]([O-:13])=[O:12])[CH2:22][CH2:21][C:19](=[O:18])[CH2:20]2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 5546572-(Trimethylsiloxy)-1,3-butadieneHCID 7096881,2-Dimethoxy-4-(2-nitrovinyl)benzene

Produkt 1

HCID 67022408(3RS,4SR)-3-(3,4-dimethoxyphenyl)-4-nitrocyclohexanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

90.0 g of 3,4-dimethoxy-ω-nitrostyrene (compound G2), 90 ml of 2-trimethylsilyloxy-1,3-butadiene and 180 ml of abs. Toluene are put in an autoclave, where the mixture is stirred at 140° C. for 2 days and then cooled. After addition of 1000 ml of ethyl acetate, 300 ml of a 2 N solution of hydrochloric acid are dropped under stirring. The phases are separated and the aqueous layer is extracted three times with dichloromethane. The combined organic extracts are washed with saturated sodium hydrogencarbonate solution, dried over magnesium sulfate and the solvents are removed under reduced pressure to give 150 g of the crude title compound. Further purification is carried out by chromatography on silica gel using petroleum ether/ethyl acetate in the ratio 1/1 as eluent to give 81.5 g (67% of theory) of the pure title compound.

Aufarbeitung

  1. temperaturecooled
  2. additionare dropped
  3. stirringunder stirring
  4. customThe phases are separated
  5. extractionthe aqueous layer is extracted three times with dichloromethane
  6. washThe combined organic extracts are washed with saturated sodium hydrogencarbonate solution
  7. dry with materialdried over magnesium sulfate
  8. customthe solvents are removed under reduced pressure
  9. customto give 150 g of the crude title compound
  10. customFurther purification

Quellen und Nachweise

ORD-Eintrag
ord-050165276fee4d8b8f320768b373a930
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829189B2

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