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

HRID 563090Notes

Reaction equation

HRID 563090 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-20321f668ac0490d88f8fba25b10ee36
Source dataset
uspto-grants-2011_11
Patent number
US08067453B2

Reaction notes

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