Water → (4-Methyl-2-(4-(trifluoromethyl)phenyl)-1,3-thiazol-5-yl)methanol

HRID 2233568Notes

Reaction equation

HRID 2233568 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[S:5][C:6]=1[C:7](O)=[O:8].O>O1CCCC1>[CH3:1][C:2]1[N:3]=[C:4]([C:10]2[CH:11]=[CH:12][C:13]([C:16]([F:19])([F:17])[F:18])=[CH:14][CH:15]=2)[S:5][C:6]=1[CH2:7][OH:8]

Participants

4

Reactant 2

HCID 962WaterHCID 27756634-Methyl-2-(4-(trifluoromethyl)phenyl)-5-thiazolecarboxylic acid

Product 1

HCID 2783005(4-Methyl-2-(4-(trifluoromethyl)phenyl)-1,3-thiazol-5-yl)methanolYield 97.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

10.0 g of 4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid were dissolved in 50 ml tetrahydrofuran under an atmosphere of argon. 69.7 ml of boran-tetrahydrofuran complex (1 molar solution in tetrahydrofuran) was added and the mixture refluxed for three hours. Water was added to the cooled reaction mixture and the solvent removed in vacuo. The residue was extracted five times with 50 ml portions of ethyl acetate. The combined extracts were dried over MgSO4. The solvent was removed in vacuo to obtain 9.3 g of [4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-yl]-methanol as a yellow solid.

Workup

  1. temperaturethe mixture refluxed for three hours
  2. customthe solvent removed in vacuo
  3. extractionThe residue was extracted five times with 50 ml portions of ethyl acetate
  4. dry with materialThe combined extracts were dried over MgSO4
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-bc23465b4e354a2fb21fb8e12ef8021b
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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