Water → HCID 12085641, compound

HRID 563087Notes

Reaction equation

HRID 563087 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:8]=[C:9]([N:20]3[CH:24]=[CH:23][N:22]=[C:21]3[CH3:25])[O:10][C:11]=2[CH2:12][CH2:13][CH2:14][C:15](OCC)=[O:16])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:8]=[C:9]([N:20]3[CH:24]=[CH:23][N:22]=[C:21]3[CH3:25])[O:10][C:11]=2[CH2:12][CH2:13][CH2:14][CH2:15][OH:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 18174680HCID 18174680, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12085641HCID 12085641, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-(5-chloro-2-thienyl)-2-(2-methyl-1-imidazolyl)-5-oxazolebutanoate (1.80 g) was dissolved in 20 ml of tetrahydrofuran, to which was added gradually lithium aluminum hydride (210 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-(5-chloro-2-thienyl)-2-(2-methyl-1-imidazolyl)-5-oxazolebutanol. Recrystallization from hexane-ethyl acetate gave pale yellow prisms (497 mg, 31%). Melting point 77-79° 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-48eddb0c94e948f1bf82101bc805dd3c
Source dataset
uspto-grants-2011_11
Patent number
US08067453B2

Reaction notes

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