Aluminium lithium hydride → 2-Methyl-2-[5-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-propan-1-ol

HRID 490731Notes

Reaction equation

HRID 490731 reaction equation
C[O:2][C:3](=O)[CH:4]([C:6]1[N:7]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[S:9][C:10]=1[CH3:11])[CH3:5].C[O:24][C:25](=O)[C:26]([CH3:44])([C:28]1[N:29]=[C:30]([C:34]2[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][CH:35]=2)[S:31][C:32]=1[CH3:33])[CH3:27].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:11][C:10]1[S:9][C:8]([C:12]2[CH:13]=[CH:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=2)=[N:7][C:6]=1[CH:4]([CH3:5])[CH2:3][OH:2].[CH3:44][C:26]([C:28]1[N:29]=[C:30]([C:34]2[CH:35]=[CH:36][C:37]([C:40]([F:42])([F:43])[F:41])=[CH:38][CH:39]=2)[S:31][C:32]=1[CH3:33])([CH3:27])[CH2:25][OH:24]

Participants

6

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 690522072-(5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-propionic acid methyl esterHCID 690582722-Methyl-2-[5-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-propionic acid methyl ester

Product 2

HCID 587656802-Methyl-2-[5-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-propan-1-olHCID 587656942-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-propionic acid methyl ester and 2-Methyl-2-[5-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-propionic acid methyl ester (10.6 g) in THF (50 mL) is added a solution of lithium aluminum hydride in THF (1.0 M, 33 mL) at 0° C. After 2 hrs, the reaction is quenched by water and sodium hydroxide, filtered, concentrated. Chromatography on silica gel yields 2-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-propan-1-ol (4.3 g) and 2-Methyl-2-[5-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-propan-1-ol (2.6 g).

Workup

  1. customthe reaction is quenched by water and sodium hydroxide
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-450307853cc043b695ffff271ee0d536
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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