Sodium sulfate decahydrate → 5-(5-Methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridylmethanol

HRID 349951Notes

Reaction equation

HRID 349951 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:22]=[C:23]([C:27](OC)=[O:28])[CH:24]=[N:25][CH:26]=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:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[N:10][C:9]=1[CH2:19][O:20][C:21]1[CH:22]=[C:23]([CH2:27][OH:28])[CH:24]=[N:25][CH:26]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 17861341Methyl 5-(5-methyl-2-phenyl-4-oxazolyl)methoxy-3-pyridinecarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 178612255-(5-Methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridylmethanolYield 91.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (1.02 g) was added to a solution of methyl 5-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridinecarboxylate (10.70 g) in tetrahydrofuran (100 ml) at 0° C., which was stirred at room temperature for 30 minutes. Sodium sulfate decahydrate (8.93 g) was added to the reaction mixture, which was stirred at room temperature for 30 minutes. The precipitate was removed by filtration, and the filtrate was concentrated. The resulting colorless crystals were collected by filtration to obtain 5-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridylmethanol (8.93 g g, yield 91%). This was recrystallized from ethyl acetate-hexane. Melting point: 111–112° C.

Workup

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

Sources & evidence

ORD record
ord-8fad39f9d56f4428bbc4e187a2125594
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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