Water → HCID 23024921, compound

HRID 349914Notes

Reaction equation

HRID 349914 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]([C:10]1[C:14]([C:15](OC)=[O:16])=[CH:13][N:12]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]3[N:29]=[C:30]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[O:31][C:32]=3[CH3:33])=[CH:22][CH:21]=2)[N:11]=1)([CH3:9])[CH3:8].O>O1CCCC1>[CH:7]([C:10]1[C:14]([CH2:15][OH:16])=[CH:13][N:12]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][CH2:27][C:28]3[N:29]=[C:30]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[O:31][C:32]=3[CH3:33])=[CH:24][CH:25]=2)[N:11]=1)([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 23024988HCID 23024988, compound

Product 1

HCID 23024921HCID 23024921, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (0.58 g) was added to a solution of methyl 3-isopropyl-1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazole-4-carboxylate (9.02 g) in tetrahydrofuran (50 ml) at 0° C., and the mixture was stirred at room temperature for 30 minutes. After water was added to the reaction mixture, the precipitate was removed by filtration and the filtrate was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and then concentrated. The residue was subjected to silica gel column chromatography, and [3-isopropyl-1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-yl]methanol (8.20 g, yield: 97%) was obtained from the fraction eluted with ethyl acetate-hexane (1:1, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 98–99° C.

Workup

  1. customthe precipitate was removed by filtration
  2. extractionthe filtrate was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4ef0e1e65565447db038b234f20a4a20
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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