Dimethyl Sulfoxide → 4-(Tert-butyldiphenylsilyloxy)cyclohexanecarbonitrile

HRID 605595Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 605595
[Si:1]([O:18][CH:19]1[CH2:24][CH2:23][CH:22]([C:25]([NH2:27])=O)[CH2:21][CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(C)=O.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C>C(Cl)Cl>[Si:1]([O:18][CH:19]1[CH2:20][CH2:21][CH:22]([C:25]#[N:27])[CH2:23][CH2:24]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 596829464-((Tert-butyl(diphenyl)silyl)oxy)cyclohexanecarboxamide

Produkt 1

HCID 189995484-(Tert-butyldiphenylsilyloxy)cyclohexanecarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 6.42 g of 4-((tert-butyl(diphenyl)silyl)oxy)cyclohexanecarboxamide and 2.39 ml of dimethylsulfoxide in 90 ml of methylene chloride was added a solution of 2.06 ml of oxalyl chloride in 10 ml of methylene chloride at −78° C., followed by stirring the reaction mixture at −78° C. for 15 minutes. To the reaction mixture was added 7.05 ml of triethylamine at −78° C., followed by stirring the reaction mixture at −78° C. for 30 minutes and then stirring at room temperature for 1.5 hours. The reaction mixture was washed with water and brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo. The obtained residue was purified by a silica gel column chromatography (eluent: hexane to hexane/ethyl acetate=4/1) to give the title compound as a pale yellow oil.

Aufarbeitung

  1. stirringby stirring the reaction mixture at −78° C. for 30 minutes
  2. stirringstirring at room temperature for 1.5 hours
  3. washThe reaction mixture was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customThe obtained residue was purified by a silica gel column chromatography (eluent: hexane to hexane/ethyl acetate=4/1)

Quellen und Nachweise

ORD-Eintrag
ord-da08dd9e6d5a4b6d9537dcf72756755e
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915263B2

Notizen zur Reaktion

Wird geladen…