Water → HCID 12085655, compound

HRID 747399Notes

Reaction equation

HRID 747399 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:21]3[CH:25]=[CH:24][N:23]=[C:22]3[CH3:26])[S:11][C:12]=2[CH2:13][CH2:14][CH2:15][C:16](OCC)=[O:17])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([N:21]3[CH:25]=[CH:24][N:23]=[C:22]3[CH3:26])[S:11][C:12]=2[CH2:13][CH2:14][CH2:15][CH2:16][OH:17])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 12085654HCID 12085654, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12085655HCID 12085655, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-thiazolebutanoate (2.00 g) was dissolved in 20 ml of tetrahydrofuran, to which was added gradually lithium aluminum hydride (195 mg) under ice-cooling. The resulting mixture was stirred for 1 hour. Water (0.5 ml) was carefully added to the reaction mixture, the resulting mixture was filtered, and the residue on the filter paper was washed with ethyl acetate. The filtrate was concentrated to give crystals of 4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-thiazolebutanol (1.28 g, 72%). Recrystallization from ethyl acetate-hexane gave pale yellow prisms. Melting point 98-99° C.

Workup

  1. temperaturecooling
  2. filtrationthe resulting mixture was filtered
  3. washthe residue on the filter paper was washed with ethyl acetate
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3bade69903ee450694af6001de377894
Source dataset
uspto-grants-2008_07
Patent number
US07396848B1

Reaction notes

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