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

HRID 1295228Notes

Reaction equation

HRID 1295228 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-].[Li+].[Al+3].[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-pyridylmethanolYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(5-methyl-2-phenyl-4-oxazolylmethoxy)-4-pyridinecarboxylate (1.95 g) in tetrahydrofuran (20 ml) was added aluminum lithium hydride (228 mg) at 0° C. and the mixture was stirred at room temperature for 30 min. Sodium sulfate 10 hydrate (1.93 g) was added to the reaction mixture and the mixture was stirred at room temperature for 30 min. The precipitate was filtered off and the filtrate was concentrated. The obtained colorless crystals were collected by filtration to give 2-(5-methyl-2-phenyl-4-oxazolylmethoxy)-4-pyridylmethanol (1.37 g, yield 77%). The crystals were recrystallized from ethyl acetate-hexane. melting point: 100–101° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 min
  2. filtrationThe precipitate was filtered off
  3. concentrationthe filtrate was concentrated
  4. filtrationThe obtained colorless crystals were collected by filtration

Sources & evidence

ORD record
ord-e3b9eaca16ba421d8728d866963dd5ee
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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