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

HRID 1294139Notes

Reaction equation

HRID 1294139 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:20]=[C:19]([C:21](OC)=[O:22])[CH:18]=[CH:17][N:16]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:20]=[C:19]([CH2:21][OH:22])[CH:18]=[CH:17][N:16]=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-pyridylmethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 2-(5-methyl-2-phenyl-4-oxazolyl)methoxy-4-pyridinecarboxylate (1.95 g) and tetrahydrofuran (20 mL) was added lithium aluminum hydride (0.228 g) under ice-cooling, and the mixture was stirred at room temperature for 30 min. Sodium sulfate 10 hydrate (1.93 g) was added to the mixture and the mixture was stirred at room temperature for 30 min. The insoluble materials were removed by filtration, and the filtrate was concentrated. The obtained crystals were recrystallized from ethyl acetate-hexane to give [2-(5-methyl-2-phenyl-4-oxazolylmethoxy)-4-pyridyl]methanol as colorless plate crystals (1.37 g, 77%). melting point: 100-101° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 30 min
  3. customThe insoluble materials were removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customThe obtained crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-24cfc1ea6b3f42f9bcd33ec9cbd0a40f
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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