Dimethyl Sulfoxide → HCID 21392721, Verbindung

HRID 461992Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 461992
S(O[CH2:12][C:13]12[CH2:20][CH2:19][C:16]([CH3:21])([CH2:17][CH2:18]1)[CH2:15][CH2:14]2)(C1C=CC(C)=CC=1)(=O)=O.[C-:22]#[N:23].[Na+].CS(C)=O>C(Cl)Cl>[CH3:21][C:16]12[CH2:15][CH2:14][C:13]([CH2:12][C:22]#[N:23])([CH2:18][CH2:17]1)[CH2:20][CH2:19]2

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 13409934HCID 13409934, Verbindung

Produkt 1

HCID 21392721HCID 21392721, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The mixture containing 0.065 mole of 4-methylbicyclo[2.2.2]oct-1-yl methanol tosylate, 0.1 mole of sodium cyanide, and 100 ml. of dimethyl sulfoxide is stirred at 70° C for 4 hours and then poured into 500 ml. of methylene chloride. The organic phase is then washed four times with water, separated and dried with anhydrous magnesium sulfate and filtered. The filtrate is then evaporated under vacuum affording an oil which is then chromatographed on silica gel eluting with 10% ethyl acetate-90%, vol., hexane affording 4-methylbicyclo[2.2.2]oct-1-yl acetonitrile.

Aufarbeitung

  1. additionpoured into 500 ml
  2. washThe organic phase is then washed four times with water
  3. customseparated
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate is then evaporated under vacuum
  7. customaffording an oil which
  8. customis then chromatographed on silica gel eluting with 10% ethyl acetate-90%, vol., hexane

Quellen und Nachweise

ORD-Eintrag
ord-a5b825c35c3b4e0cb867ed122f472847
Quelldatensatz
uspto-grants-1977_12
Patentnummer
US04064258

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