HCID 11652360, compound → (4-Methyl-2-(4-(trifluoromethyl)phenyl)-1,3-thiazol-5-yl)methanol

HRID 1295461Notes

Reaction equation

HRID 1295461 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[S:5][C:6]=1[C:7](OC)=[O:8].[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[CH3:1][C:2]1[N:3]=[C:4]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:15][CH:16]=2)[S:5][C:6]=1[CH2:7][OH:8]

Participants

4

Reactant 2

HCID 11652360HCID 11652360, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 2783005(4-Methyl-2-(4-(trifluoromethyl)phenyl)-1,3-thiazol-5-yl)methanolYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Methyl 4-methyl-2-[4-(trifluoromethyl)phenyl]]thiazole-5-carboxylate (20.0 g, 66.4 mmol) obtained from Example 1 was dissolved in anhydrous dichloromethane (500 ml) under nitrogen atmosphere, and the reaction mixture was cooled to −78° C. Diisobutyl aluminum hydride (DIBAL-H, 166 ml, 1.0 M hexane solution, 2.5 eq.) was slowly added to the solution for 30 minutes, and the mixture was reacted for another 30 minutes at the same temperature. Subsequently, the temperature was raised to −10° C. and reacted for 30 minutes. After completion of the reaction, an excessive diisobutyl aluminum hydride was removed by ethyl acetate. The resultant residue was extracted by 10% sulfuric acid and ethyl acetate, followed by drying over magnesium sulfate. The resultant mixture was purified on silica flash column, followed by evaporation under reduced pressure to thereby yield 17.5 g of the title compound (yield: 96.4%).

Workup

  1. customthe mixture was reacted for another 30 minutes at the same temperature
  2. temperatureSubsequently, the temperature was raised to −10° C.
  3. customreacted for 30 minutes
  4. customAfter completion of the reaction
  5. customan excessive diisobutyl aluminum hydride was removed by ethyl acetate
  6. extractionThe resultant residue was extracted by 10% sulfuric acid and ethyl acetate
  7. dry with materialby drying over magnesium sulfate
  8. customThe resultant mixture was purified on silica flash column

Sources & evidence

ORD record
ord-3ffa4280908c40368305840287217973
Source dataset
uspto-grants-2007_07
Patent number
US07241901B2

Reaction notes

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