Imidazole → 2-[3-(Tert-butyldimethylsilanyloxy)-4,4,4-trifluorobutyl]pyridine

HRID 1070978Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1070978
[F:1][C:2]([F:14])([F:13])[CH:3]([OH:12])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].N1C=CN=C1>ClCCl.CN(C)C1C=CN=CC=1>[Si:15]([O:12][CH:3]([C:2]([F:1])([F:13])[F:14])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Komponenten

6

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 223986331,1,1-Trifluoro-4-pyridin-2-ylbutan-2-ol

Produkt 1

HCID 223986342-[3-(Tert-butyldimethylsilanyloxy)-4,4,4-trifluorobutyl]pyridineAusbeute 89,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 700 mg (3.4 mmol) of 1,1,1-trifluoro-4-pyridin-2-ylbutan-2-ol in 10 mL of dichloromethane was treated with 616 mg (4.1 mmol, 1.2 eq.) of tert-butyldimethylsilyl chloride, 697 mg (10.2 mmol, 3.0 eq.) of imidazole and 415 ng (3.4 mmol) of 4-dimethylaminopyridine at 0° C. The resulting mixture was allowed to warm to room temperature and was stirred for 36 hours. Then the mixture was concentrated and the residue was purified by flash chromatography to give 970 mg (89%) of 2-[3-(tert-butyldimethylsilanyloxy)-4,4,4-trifluorobutyl]pyridine as a colorless oil.

Aufarbeitung

  1. concentrationThen the mixture was concentrated
  2. customthe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3c2716a9418e4c3bae47909565b9648f
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06903215B2

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