Water → HCID 69424039, compound

HRID 349912Notes

Reaction equation

HRID 349912 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:12]1[O:13][C:14]([CH3:57])=[C:15]([CH2:17][O:18][C:19]2[CH:56]=[CH:55][C:22]([CH2:23][N:24]3[CH:28]=[C:27]([C:29](OCC)=[O:30])[C:26]([O:34][CH2:35][C:36]4[CH:41]=[CH:40][C:39]([O:42][CH2:43][C:44]5[N:45]=[C:46]([C:50]6[O:51][CH:52]=[CH:53][CH:54]=6)[O:47][C:48]=5[CH3:49])=[CH:38][CH:37]=4)=[N:25]3)=[CH:21][CH:20]=2)[N:16]=1.O>O1CCCC1>[O:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:12]1[O:13][C:14]([CH3:57])=[C:15]([CH2:17][O:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:23][N:24]3[CH:28]=[C:27]([CH2:29][OH:30])[C:26]([O:34][CH2:35][C:36]4[CH:37]=[CH:38][C:39]([O:42][CH2:43][C:44]5[N:45]=[C:46]([C:50]6[O:51][CH:52]=[CH:53][CH:54]=6)[O:47][C:48]=5[CH3:49])=[CH:40][CH:41]=4)=[N:25]3)=[CH:55][CH:56]=2)[N:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 69423039HCID 69423039, compound

Product 1

HCID 69424039HCID 69424039, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (0.98 g) was added to a solution of ethyl 1-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]benzyl]-3-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]benzyloxy]-1H-pyrazole-4-carboxylate (19.16 g) in tetrahydrofuran (75 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-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]benzyl]-3-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]benzyloxy]-1H-pyrazol-4-yl]methanol (17.25 g, yield: 96%). This was recrystallized from ethyl acetate-hexane. Melting point: 80–81° 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-476384dbde8546a58c0aa8f4e461ac9d
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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