Tetrabutylammonium Fluoride → 1,1,1-Trifluoro-4-methyl-4-pyridin-2-ylpentan-2-ol

HRID 1988158Notes

Reaction equation

HRID 1988158 reaction equation
[Si]([O:8][CH:9]([C:20]([F:23])([F:22])[F:21])[CH2:10][C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)([CH3:13])[CH3:12])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[F:23][C:20]([F:21])([F:22])[CH:9]([OH:8])[CH2:10][C:11]([CH3:12])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[CH3:13]

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 223984572-[3-(Tert-butyldimethylsilanyloxy)-4,4,4-trifluoro-1,1-dimethylbutyl]pyridine

Product 1

HCID 223985011,1,1-Trifluoro-4-methyl-4-pyridin-2-ylpentan-2-olYield 99.6%

Procedure

A mixture of 550 mg (1.58 mmol) of 2-[3-(tert-butyldimethylsilanyloxy)-4,4,4-trifluoro-1,1-dimethylbutyl]pyridine in 4.5 mL (4.5 mmol) of tetrabutylammonium fluoride (1.0 M solution in THF) was stirred at room temperature for 2 hours. The mixture was concentrated in vacuo and the residue was purified by flash chromatography to give 367 mg (99%) of 1,1,1-trifluoro-4-methyl-4-pyridin-2-ylpentan-2-ol as a light yellow oil.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-180886a714f94a3fb7195cf28fced4c4
Source dataset
uspto-grants-2009_06
Patent number
US07553966B2

Reaction notes

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