Sodium Hydroxide → 2-(2-Methyl-4-phenyl-1,3-oxazol-5-yl)ethan-1-ol

HRID 1982424Notes

Reaction equation

HRID 1982424 reaction equation
[OH-].[Na+].C([O:6][CH2:7][CH2:8][C:9]1[O:13][C:12]([CH3:14])=[N:11][C:10]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=O)C>CO.O>[OH:6][CH2:7][CH2:8][C:9]1[O:13][C:12]([CH3:14])=[N:11][C:10]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 23316609HCID 23316609, compound

Product 1

HCID 233165962-(2-Methyl-4-phenyl-1,3-oxazol-5-yl)ethan-1-ol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2N Sodium hydroxide (40 ml) was added to a solution of 5-(2-acetoxyethyl)-2-methyl-4-phenyloxazole (16.6 g) in methanol (40 ml) and the mixture was stirred for 30 minutes, diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was then distilled off and the residue wwas purified by silica gel chromatography (silica gel: 190 g, eluent: isopropyl ether) to give an oil of 5-(2-hydroxyethyl)-2-methyl-4-phenyloxazole, yield 11.7 g (84.8%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was then distilled off
  5. customthe residue wwas purified by silica gel chromatography (silica gel: 190 g, eluent: isopropyl ether)

Sources & evidence

ORD record
ord-decb03e0d1054a45986c3fa683b198e9
Source dataset
uspto-grants-1986_06
Patent number
US04596816

Reaction notes

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