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

HRID 2080580Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2080580
[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-b85b06f9227044caa59e92858570b273
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932392B2

Notizen zur Reaktion

Wird geladen…