Tetrabutylammonium Fluoride → 4-[3-(Trifluoromethyl)-1H-pyrazol-1-yl]cyclohexanol

HRID 1025681Notes

Reaction equation

HRID 1025681 reaction equation
[Si]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([N:15]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[N:16]2)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C(Cl)Cl>[F:23][C:20]([F:21])([F:22])[C:17]1[CH:18]=[CH:19][N:15]([CH:12]2[CH2:11][CH2:10][CH:9]([OH:8])[CH2:14][CH2:13]2)[N:16]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 595560591-(4-{[tert-Butyl(dimethyl)silyl]oxy}cyclohexyl)-3-(trifluoromethyl)-1H-pyrazole

Product 1

HCID 595561464-[3-(Trifluoromethyl)-1H-pyrazol-1-yl]cyclohexanolYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

The intermediate (0.56 g, 1.6 mmol) from step C was dissolved in CH2Cl2 (10 mL) and to it was added a 1 M solution of TBAF in CH2Cl2 (5 mL). After being stirred at room temperature for 2 hours, the solution was diluted with CH2Cl2. The resulting solution was washed with brine, dried over MgSO4 and concentrated. Purification on silica gel eluting with 2:1 EtOAc/hexanes provided the title compound (0.27 g, 71%) as an oil. MS calculated (M+H)+ 235, found 235.

Workup

  1. washThe resulting solution was washed with brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customPurification on silica gel eluting with 2:1 EtOAc/hexanes

Sources & evidence

ORD record
ord-9b993db75b1446639721d845d219ec4e
Source dataset
uspto-grants-2014_05
Patent number
US08729063B2

Reaction notes

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