Sodium Chloride → Trans-3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]5-cyanocyclohexanone

HRID 1758154Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1758154
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:23])([CH3:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=[CH:11][C:10]=1[CH:24]1[CH2:29][C:28](=[O:30])[CH:27]=[CH:26][CH2:25]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C.[C-:37]#[N:38].[K+].[Cl-].[Na+]>CCOCC.C(O)C.O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:22])([CH3:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=[CH:11][C:10]=1[C@H:24]1[CH2:25][C@H:26]([C:37]#[N:38])[CH2:27][C:28](=[O:30])[CH2:29]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

8

Edukt 4

HCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 9032Potassium Cyanide2×HCID 127882935-(2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-2-cyclohexen-1-one

Produkt 1

HCID 13105260Trans-3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]5-cyanocyclohexanoneAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a refluxing solution of 3.99 g. (9.87 mmole) of 5-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-2-cyclohexen-1-one in 6.65 ml. of ethyl acetate was added a hot solution of 800 mg. (11.9 mmole) of potassium cyanide in 2 ml. water and 2.3 ml. ethanol. The reaction was refluxed 2 hours and then another 2.74 mmole of potassium cyanide added. The reaction was refluxed one hour longer and then cooled and added to 400 ml. saturated sodium chloride-400 ml. ether. The ether extract was dried over magnesium sulfate and evaporated to yield an oil. The crude oil was purified via column chromatography on 160 g. of silica gel eluted with 10% acetone-hexane to yield 3.02 g. (71%) of the title compound.

Aufarbeitung

  1. temperatureThe reaction was refluxed 2 hours
  2. temperatureThe reaction was refluxed one hour longer
  3. temperaturecooled
  4. additionadded to 400 ml
  5. extractionThe ether extract
  6. dry with materialwas dried over magnesium sulfate
  7. customevaporated
  8. customto yield an oil
  9. customThe crude oil was purified via column chromatography on 160 g
  10. washof silica gel eluted with 10% acetone-hexane
  11. customto yield 3.02 g

Quellen und Nachweise

ORD-Eintrag
ord-44d28fe791964f57af8467544c5d209a
Quelldatensatz
uspto-grants-1983_02
Patentnummer
US04371720

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