Triethylsilane → 4-[1-(tert-butyldimethylsilanyloxy)-2-(1-trityl-1H-imidazol-4-ylmethoxy)ethyl]benzonitrile

HRID 1095306Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1095306
FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[Si:13]([O:20][CH:21]([C:50]1[CH:55]=[CH:54][C:53]([C:56]#[N:57])=[CH:52][CH:51]=1)[C:22]([O:24][CH2:25][C:26]1[N:27]=[CH:28][N:29]([C:31]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:30]=1)=O)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C([SiH](CC)CC)C>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[Si:13]([O:20][CH:21]([C:50]1[CH:55]=[CH:54][C:53]([C:56]#[N:57])=[CH:52][CH:51]=1)[CH2:22][O:24][CH2:25][C:26]1[N:27]=[CH:28][N:29]([C:31]([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:30]=1)([C:16]([CH3:19])([CH3:17])[CH3:18])([CH3:15])[CH3:14]

Komponenten

6

Edukt 3

HCID 12052TriethylsilaneHCID 65367Trimethylsilyl triflateHCID 866329551-trityl-1H-imidazol-4-ylmethyl (tert-butyldimethylsilyloxy)(4-cyanophenyl)acetate

Produkt 1

HCID 667816954-[1-(tert-butyldimethylsilanyloxy)-2-(1-trityl-1H-imidazol-4-ylmethoxy)ethyl]benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

A solution of 1.27 mmol of titanium tetrachloride in 1.5 ml of dichloromethane is added to a solution of 2.61 mmol of trimethylsilyl trifluoromethanesulphonate in 1 ml of dichloromethane at 0° C. The mixture is stirred at room temperature for 4 hours and then cooled to 0° C. A solution of 0.83 mmol of 1-trityl-1H-imidazol-4-ylmethyl (tert-butyldimethylsilyloxy)(4-cyanophenyl)acetate and 4.17 mmol of triethylsilane in 2 ml of dichloromethane is added, and the reaction mixture is stirred at room temperature for 20 hours. The reaction mixture is poured into ice-water and extracted with ethyl acetate (2×). The combined organic phases are washed with water and brine, dried with sodium sulphate and evaporated. The title compound is identified from the residue on the basis of the Rf by flash chromatography (SiO2 60 F).

Aufarbeitung

  1. temperaturecooled to 0° C
  2. stirringthe reaction mixture is stirred at room temperature for 20 hours
  3. extractionextracted with ethyl acetate (2×)
  4. washThe combined organic phases are washed with water and brine
  5. dry with materialdried with sodium sulphate
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-a2bd8ce0cfed49ae89c52f9b933aeaba
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138176B2

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