Diethyl Ether → [1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-yl]methanol

HRID 349933Notes

Reaction equation

HRID 349933 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:37]=[CH:36][C:24]([CH2:25][N:26]2[CH:30]=[C:29]([C:31](OCC)=[O:32])[CH:28]=[N:27]2)=[CH:23][CH:22]=1.C(OCC)C.[OH-].[Na+]>O1CCCC1>[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[N:10][C:9]=1[CH2:19][O:20][C:21]1[CH:37]=[CH:36][C:24]([CH2:25][N:26]2[CH:30]=[C:29]([CH2:31][OH:32])[CH:28]=[N:27]2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 23024913ethyl 1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazole-4-carboxylate

Product 1

HCID 69422348[1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-yl]methanolYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (323 mg) was added to a mixture of ethyl 1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazole-4-carboxylate (3.55 g), diethyl ether (25 ml), and tetrahydrofuran (25 ml) at 0° C., and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into a 1N aqueous sodium hydroxide solution, which was extracted with diethyl ether. The diethyl ether layer was washed with water and then with saturated aqueous sodium chloride solution, dried (MgSO4), and then concentrated. The crystals obtained were filtrated to obtain [1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-yl]methanol (2.93 g, yield: 92%). This was recrystallized from ethyl acetate-hexane. Melting point: 100–101° C.

Workup

  1. extractionwas extracted with diethyl ether
  2. washThe diethyl ether layer was washed with water
  3. dry with materialwith saturated aqueous sodium chloride solution, dried (MgSO4)
  4. concentrationconcentrated
  5. customThe crystals obtained
  6. filtrationwere filtrated

Sources & evidence

ORD record
ord-311fe1e0398f47d5bdea9a418ce10f37
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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