(Trifluoromethyl)trimethylsilane → HCID 67130392, compound

HRID 1403692Notes

Reaction equation

HRID 1403692 reaction equation
[S:1]1[CH:5]=[C:4]([CH:6]=[O:7])[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:4]1[N:3]=[CH:2][S:1][CH:5]=1)[OH:7]

Participants

5

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 2763214Thiazole-4-carboxaldehyde

Product 1

HCID 67130392HCID 67130392, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The method described in Example 4 (step 4.5.) is followed. Starting from 1 g (8.84 mmol) of thiazole-4-carboxaldehyde, 0.10 ml (0.10 mmol) of a 1M solution of tetrabutylammonium fluoride in THF and 1.38 g (9.72 mmol) of trifluoromethyltrimethylsilane (TMS-CF3), and after chromatography on silica gel, eluting with a 98/2 mixture of dichloromethane and methanol, gives 0.54 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-ed0dc42b9a224bed9350670063b1ad5f
Source dataset
uspto-grants-2014_12
Patent number
US08912218B2

Reaction notes

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