Phosphorus oxychloride → 5-Methyl-2-pentyl-4-phenyl-1,3-oxazole

HRID 1982437Notes

Reaction equation

HRID 1982437 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]([NH:13][CH:14]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:15](=[O:17])[CH3:16])(=O)[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]>C1(C)C=CC=CC=1>[CH3:16][C:15]1[O:17][C:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[N:13][C:14]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 13293301N-(2-Oxo-1-phenylpropyl)hexanamide

Product 1

HCID 233165955-Methyl-2-pentyl-4-phenyl-1,3-oxazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Phosphorous oxychloride (5.58 ml) was added to a solution of 1-hexanoylamino-1-phenyl-2-propanone (4.94 g) in toluene (50 ml) and the solution was refluxed with stirring for 40 minutes. The solvent was distilled off and water was added to the residue. The mixture was neutralized with potassium carbonate and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was then distilled off and the residue was purified by silica gel chromatography [silice gel: 80 g; eluent: hexane-ethyl ether (4:1)] to give an oil of 5-methyl-2-pentyl-4-phenyloxazole, yield 4.25 g (92.8%).

Workup

  1. temperaturethe solution was refluxed
  2. distillationThe solvent was distilled off
  3. additionwater was added to the residue
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was then distilled off
  8. customthe residue was purified by silica gel chromatography [silice gel: 80 g; eluent: hexane-ethyl ether (4:1)]

Sources & evidence

ORD record
ord-3af3bec9a2084cfabd07eed7aea8bb44
Source dataset
uspto-grants-1986_06
Patent number
US04596816

Reaction notes

Loading…