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

HRID 2080580Notes

Reaction equation

HRID 2080580 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

HCID 223986342-[3-(Tert-butyldimethylsilanyloxy)-4,4,4-trifluorobutyl]pyridineYield 89.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-b85b06f9227044caa59e92858570b273
Source dataset
uspto-grants-2011_04
Patent number
US07932392B2

Reaction notes

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