Sodium sulfate decahydrate → 2-(5-Methyl-2-phenyl-4-oxazolylmethoxy)-4-pyridylmethanol

HRID 349948Notes

Reaction equation

HRID 349948 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:26]=[C:25]([C:27](OC)=[O:28])[CH:24]=[CH:23][N:22]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>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:26]=[C:25]([CH2:27][OH:28])[CH:24]=[CH:23][N:22]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 17861336Methyl 2-(5-methyl-2-phenyl-4-oxazolyl)methoxy-4-pyridinecarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 178613752-(5-Methyl-2-phenyl-4-oxazolylmethoxy)-4-pyridylmethanolYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (228 mg) was added to a solution of methyl 2-(5-methyl-2-phenyl-4-oxazolylmethoxy)-4-pyridinecarboxylate (1.95 g) in tetrahydrofuran (20 ml) at 0° C., which was stirred at room temperature for 30 minutes. Sodium sulfate decahydrate (1.93 g) was added to the reaction mixture, which was stirred at room temperature for 30 minutes. The precipitates were removed by filtration, the filtrate was concentrated. The resulting colorless crystals were collected by filtration to obtain 2-(5-methyl-2-phenyl-4-oxazolylmethoxy)-4-pyridylmethanol (1.37 g, yield 77%). This was recrystallized from ethyl acetate-hexane. Melting point: 100–101° C.

Workup

  1. stirringwas stirred at room temperature for 30 minutes
  2. customThe precipitates were removed by filtration
  3. concentrationthe filtrate was concentrated
  4. filtrationThe resulting colorless crystals were collected by filtration

Sources & evidence

ORD record
ord-1e87c65db03f4f78831acb664f1c0722
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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