Methyl iodide → 3-(Tertbutyldimethylsilyloxy)-1-(5-methyl-[1,2,4]-triazol-1-yl)propane

HRID 454113Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 454113
[C:1]([Si:5]([CH3:16])([CH3:15])[O:6][CH2:7][CH2:8][CH2:9][N:10]1[CH:14]=[N:13][CH:12]=[N:11]1)([CH3:4])([CH3:3])[CH3:2].[CH2:17]([Li])CCC.CI.[Cl-].[NH4+]>CN(C=O)C.CCOCC.C(OCC)(=O)C>[C:1]([Si:5]([CH3:16])([CH3:15])[O:6][CH2:7][CH2:8][CH2:9][N:10]1[C:14]([CH3:17])=[N:13][CH:12]=[N:11]1)([CH3:2])([CH3:4])[CH3:3]

Komponenten

8

Edukt 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 220308973-(Tertbutyldimethylsilyloxy)-1-(1,2,4-triazol-1-yl)propaneHCID 178418339Butyllithium

Produkt 1

HCID 220308553-(Tertbutyldimethylsilyloxy)-1-(5-methyl-[1,2,4]-triazol-1-yl)propaneAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

To a solution of 3-(tertbutyldimethylsilyloxy)-1-(1,2,4-triazol-1-yl)propane (7 g, 29 mmol) in DMF (100 ml) cooled at −70° C. was added 2.5M n-butyllithium (17.4 ml) over 45 minutes. After stirring for 90 minutes at −70° C., methyl iodide (3.6 ml, 58 mmol) was added. After stirring for 2 hours at ambient temperature, the mixture was poured onto saturated ammonium chloride. The mixture was then diluted with ether and ethyl acetate. The organic layer was separated, washed with aqueous sodium thiosulphate followed by brine, dried (MgSO4) and evaporated to give 3-(tertbutyldimethylsilyloxy)-1-(5-methyl-[1,2,4]-triazol-1-yl)propane (7.3 g, 98%).

Aufarbeitung

  1. stirringAfter stirring for 2 hours at ambient temperature
  2. customThe organic layer was separated
  3. washwashed with aqueous sodium thiosulphate
  4. dry with materialdried (MgSO4)
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d38978b4d4294d619f9d4a4a3c7f0456
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492560B2

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