Water → HCID 23024927, compound

HRID 349910Notes

Reaction equation

HRID 349910 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:9]=1[CH2:19][O:20][C:21]1[CH:59]=[CH:58][C:24]([CH2:25][N:26]2[CH:30]=[C:29]([C:31](OCC)=[O:32])[C:28]([O:36][CH2:37][C:38]3[CH:43]=[CH:42][C:41]([O:44][CH2:45][C:46]4[N:47]=[C:48]([C:52]5[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=5)[O:49][C:50]=4[CH3:51])=[CH:40][CH:39]=3)=[N:27]2)=[CH:23][CH:22]=1.O>O1CCCC1>[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:9]=1[CH2:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([CH2:25][N:26]2[CH:30]=[C:29]([CH2:31][OH:32])[C:28]([O:36][CH2:37][C:38]3[CH:43]=[CH:42][C:41]([O:44][CH2:45][C:46]4[N:47]=[C:48]([C:52]5[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=5)[O:49][C:50]=4[CH3:51])=[CH:40][CH:39]=3)=[N:27]2)=[CH:58][CH:59]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 23024781HCID 23024781, compound

Product 1

HCID 23024927HCID 23024927, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (2.03 g) was added to a solution of ethyl 1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-3-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxy]-1H-pyrazole-4-carboxylate (40.00 g) in tetrahydrofuran (150 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 crystals obtained were collected by filtration to yield [1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-3-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxy]-1H-pyrazol-4-yl]methanol (35.91 g, yield: 95%). This was recrystallized from tetrahydrofuran-hexane. Melting point: 157–158° 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
  6. customThe crystals obtained
  7. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-2719bf04c14f42a091e5dd38e23544d3
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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