2-(4-Trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester → {2-[4-(Trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methanol

HRID 1393076Notes

Reaction equation

HRID 1393076 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[N:8][CH:7]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:20][C:17]([F:18])([F:19])[C:14]1[CH:13]=[CH:12][C:11]([C:9]2[S:10][C:6]([CH2:4][OH:3])=[CH:7][N:8]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 210512492-(4-Trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 22647407{2-[4-(Trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methanolYield 101.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester (5.122 g, 17.00 mmol) in THF (85 ml) was added dropwise with cooling (15° C.) LAH (1M in THF, 17.34 ml, 17.34 mmol). The resulting mixture was stirred 30 min at RT and the reaction was quenched at ca 15° C. by the cautious addition of 20 ml saturated aqueous NH4Cl solution. The precipitate was filtered, washed with THF, evaporated and suspended in CH2Cl2. Na2SO4 was added and the organic phase filtered and evaporated to give 4.46 g (quantitative) of [2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-methanol as a yellow crytalline residue, MS: 259 (M+), MP: 95-98° C., dec.

Workup

  1. customthe reaction was quenched at ca 15° C. by the cautious addition of 20 ml saturated aqueous NH4Cl solution
  2. filtrationThe precipitate was filtered
  3. washwashed with THF
  4. customevaporated
  5. additionNa2SO4 was added
  6. filtrationthe organic phase filtered
  7. customevaporated

Sources & evidence

ORD record
ord-0bfaec6c4a354c89adc66d121e0fdc4d
Source dataset
uspto-grants-2008_03
Patent number
US07345067B2

Reaction notes

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