4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester → (4-Methyl-2-(4-(trifluoromethyl)phenyl)-1,3-thiazol-5-yl)methanol

HRID 460013

Reaction equation

HRID 460013 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[N:9]=[C:10]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[S:11][C:12]=1[C:13](OCC)=[O:14]>O1CCCC1>[CH3:7][C:8]1[N:9]=[C:10]([C:18]2[CH:19]=[CH:20][C:21]([C:24]([F:27])([F:25])[F:26])=[CH:22][CH:23]=2)[S:11][C:12]=1[CH2:13][OH:14]

Participants

4

Reactant 2

HCID 27372104-Methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl esterHCID 21226445Aluminium lithium hydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a well stirred solution of lithium aluminium hydride (1.52 g) in dry tetrahydrofuran (50 ml) at 0° C., was slowly added a solution of ethyl 4-methyl-2-[4-(trifluoromethyl)phenyl]-thiazole-5-carboxylate (12.6 g) in dry tetrahydrofuran (50 ml). The mixture was stirred at room temperature for 2 hours. The reaction was quenched by slow addition at 0° C. of water (2 ml), 5N NaOH (2 ml) and water (6 ml). The precipitate was filtered, washed with ethyl acetate, methanol, dichloromethane and tetrahydrofuran. After evaporation, a yellow solid was obtained, that was crystallized from methanol-water to afford the title compound as a yellow solid.

Workup

  1. customThe reaction was quenched by slow addition at 0° C. of water (2 ml), 5N NaOH (2 ml) and water (6 ml)
  2. filtrationThe precipitate was filtered
  3. washwashed with ethyl acetate, methanol, dichloromethane and tetrahydrofuran
  4. customAfter evaporation
  5. customa yellow solid was obtained
  6. customthat was crystallized from methanol-water

Sources & evidence

ORD record
ord-fcce98f8ec4e465b835e6ebfda960211
Source dataset
uspto-grants-2007_03
Patent number
US07196107B2

Linked notes

Loading…