(Trifluoromethyl)trimethylsilane → α-(Trifluoromethyl)-5-thiazolemethanol

HRID 1403694Notes

Reaction equation

HRID 1403694 reaction equation
[S:1]1[C:5]([CH:6]=[O:7])=[CH:4][N:3]=[CH:2]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:26][C:27]([Si](C)(C)C)([F:29])[F:28]>C1COCC1>[F:26][C:27]([F:29])([F:28])[CH:6]([C:5]1[S:1][CH:2]=[N:3][CH:4]=1)[OH:7]

Participants

5

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 27735771,3-Thiazole-5-carbaldehyde

Product 1

HCID 67130512α-(Trifluoromethyl)-5-thiazolemethanolYield 68.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The method described in Example 4 (step 4.5.) is followed. Starting from 2 g (17.68 mmol) of thiazole-5-carboxaldehyde, 0.88 ml (0.88 mmol) of a 1M solution of tetrabutylammonium fluoride in THF and 2.765 g (19.44 mmol) of trifluoromethyltrimethylsilane (TMS-CF3), and after chromatography on silica gel, eluting with a 98/2 mixture of dichloromethane and methanol, gives 2.23 g of pure product in the form of a colourless oil.

Workup

  1. washafter chromatography on silica gel, eluting with a 98/2 mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-a1024248a7f14ff8b9fd1e47c99a1d84
Source dataset
uspto-grants-2014_12
Patent number
US08912218B2

Reaction notes

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