(Trifluoromethyl)trimethylsilane → HCID 59295451, compound

HRID 2233295Notes

Reaction equation

HRID 2233295 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:9]2[CH:10]=[N:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=2)[S:5][C:6]=1[CH:7]=[O:8].CC1N=C(C2C=NC([C:33]([F:36])([F:35])[F:34])=CC=2)SC=1CO.FC([Si](C)(C)C)(F)F.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:34][C:33]([F:36])([F:35])[CH:7]([C:6]1[S:5][C:4]([C:9]2[CH:10]=[N:11][C:12]([C:15]([F:18])([F:16])[F:17])=[CH:13][CH:14]=2)=[N:3][C:2]=1[CH3:1])[OH:8]

Participants

6

Reactant 4

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 59295400HCID 59295400, compoundHCID 59295476HCID 59295476, compound

Product 1

HCID 59295451HCID 59295451, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cooled solution of 2.0 g 4-Methyl-2-(6-trifluoromethyl-pyridin-3-yl)-thiazole-5-carbaldehyde (derived from [4-Methyl-2-(6-trifluoromethyl-pyridin-3-yl)-thiazol-5-yl]-methanol according to the method described for 4-Methyl-2-(trans-1,4-trifluoromethyl-cyclohexyl)-thiazole-5-carbaldehyde) and 1.09 ml (trifluoromethyl)trimethylsilane in 10 ml tetrahydrofuran were added 100 mg tetrabutylammoniumfluoride. The reaction mixture was stirred at room temperature for thirty minutes. Then 20 ml 2N HCL were added and the mixture stirred at room temperature for thirty minutes. The mixture was extracted three times with portions of 50 ml ethyl acetate. The combined organic layers were dried over MgSO4. The solvent was evaporated in vacuo to obtain 1.5 g 2,2,2-Trifluoro-1-[4-methyl-2-(6-trifluoromethyl-pyridin-3-yl)-thiazol-5-yl]-ethanol as a solid.

Workup

  1. additionThen 20 ml 2N HCL were added
  2. stirringthe mixture stirred at room temperature for thirty minutes
  3. extractionThe mixture was extracted three times with portions of 50 ml ethyl acetate
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-6cb903c0da5d4eefa0d58a6e2d9ec3e3
Source dataset
uspto-grants-2010_05
Patent number
US07709481B2

Reaction notes

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