Water → 4-(4-Fluorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolebutanol

HRID 747433Notes

Reaction equation

HRID 747433 reaction equation
[F: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])[O: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>[F: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])[O: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 18174712HCID 18174712, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 181747334-(4-Fluorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolebutanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-(4-fluorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolebutanoate (2.31 g) was dissolved in 20 ml of tetrahydrofuran, to which was added gradually lithium aluminum hydride (269 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-fluorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolebutanol. Recrystallization from ethyl acetate gave pale yellow prisms (885 mg, 47%). Melting point 97-98° 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-bd7f722e2e96413e88d6b9956a5e6643
Source dataset
uspto-grants-2008_07
Patent number
US07396848B1

Reaction notes

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