Tetrabutylammonium Fluoride → 4-Hydroxy-2-(2-trifluoromethylphenyl)butyronitrile

HRID 406357Notes

Reaction equation

HRID 406357 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]([F:23])([F:22])[F:21])[C:12]#[N:13])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:8][CH2:9][CH2:10][CH:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]([F:21])([F:22])[F:23])[C:12]#[N:13]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 666188214-(Tert-butyldimethylsilyloxy)-2-(2-trifluoromethylphenyl)butyronitrile

Product 1

HCID 667786674-Hydroxy-2-(2-trifluoromethylphenyl)butyronitrileYield 92.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(tert-Butyldimethylsilyloxy)-2-(2-trifluoromethylphenyl)butyronitrile (5 g) was dissolved in tetrahydrofuran (70 mL). Tetrabutylammonium fluoride (1 M solution in tetrahydrofuran) (18 mL) was added and the mixture was stirred at room temperature for 4.5 hours. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (3.1 g). The property values of the compound are as follows.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2ade4aaa6c7f46068da0c4a2a0929f08
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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