Potassium Carbonate → HCID 178434805, Verbindung

HRID 2050469Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2050469
ClC1C=CC=C(C(OO)=[O:9])C=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18]([C@H:23]1[CH2:28][CH2:27][C@H:26]([C:29]2[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=2)[CH2:25][CH2:24]1)[CH2:19][CH:20]=[CH:21][CH3:22]>C(Cl)Cl>[O:9]1[CH:21]([CH3:22])[CH:20]1[CH2:19][CH2:18][C@H:23]1[CH2:24][CH2:25][C@H:26]([C:29]2[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=2)[CH2:27][CH2:28]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acid2×HCID 178444326HCID 178444326, Verbindung

Produkt 1

HCID 178434805HCID 178434805, VerbindungAusbeute 99,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 4.49 g of 90% m-chloroperbenzoic acid in 100 ml of methylene chloride was treated with 11.3 g of powdered potassium carbonate. The mixture was treated dropwise at 0° C. within 5 minutes with a solution of 5.93 g of p-[trans-4-(3-pentenyl)cyclohexyl]benzonitrile in 20 ml of methylene chloride and stirred at room temperature for 2 hours. The mixture was subsequently treated with a further 4.49 g of 90% m-chloroperbenzoic acid and the resulting mixture was stirred further. After a total of 70 hours, the mixture was partitioned three times in methylene chloride/10% sodium thiosulphate solution. The organic extracts were washed with sodium thiosulphate solution and water, dried over magnesium sulphate, filtered and concentrated. Chromatographic separation of the resulting, light yellowish oil (6.3 g) on silica gel with ethyl acetate/petroleum ether (vol. 10:90) gave 6.27 g (99.5%) of p-[trans-4-(3,4-epoxypentyl)cyclohexyl]benzonitrile as a colourless oil.

Aufarbeitung

  1. stirringthe resulting mixture was stirred further
  2. customAfter a total of 70 hours, the mixture was partitioned three times in methylene chloride/10% sodium thiosulphate solution
  3. washThe organic extracts were washed with sodium thiosulphate solution and water
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customChromatographic separation of the resulting, light yellowish oil (6.3 g) on silica gel with ethyl acetate/petroleum ether (vol. 10:90)

Quellen und Nachweise

ORD-Eintrag
ord-a2fc1a6844e14f9494210c9d2dd63c87
Quelldatensatz
uspto-grants-1991_05
Patentnummer
US05013478

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