Sodium Hydroxide → HCID 17861327, compound

HRID 349980Notes

Reaction equation

HRID 349980 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:16]=[CH:17][C:18]([CH2:21][O:22]C(=O)C)=[N:19][CH:20]=1.[OH-].[Na+]>CO>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][OH:22])=[N:19][CH:20]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 17861268HCID 17861268, compound

Product 1

HCID 17861327HCID 17861327, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of [5-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-pyridylmethyl]acetate (18.00 g), 1N aqueous sodium hydroxide solution (75 ml) and methanol (100 ml) was stirred at room temperature for 3 hours, and concentrated. The residue was dissolved in ethyl acetate, which was washed with water and saturated aqueous sodium chloride solution. The organic layer was dried (MgSO4) and concentrated. The resulting colorless crystals were collected by filtration to obtain 5-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-pyridylmethanol (14.29 g, yield 91%). This was recrystallized from ethyl acetate-hexane. Melting point: 125–126° C.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwhich was washed with water and saturated aqueous sodium chloride solution
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. filtrationThe resulting colorless crystals were collected by filtration

Sources & evidence

ORD record
ord-49a1d65919a749d8b1f4616cae684a3f
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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