Phosphorus oxychloride → HCID 13282959, compound

HRID 746032Notes

Reaction equation

HRID 746032 reaction equation
[CH3:1][C:2]1([C:8]([NH:10][CH:11]([C:17](=[O:19])[CH3:18])[CH2:12][C:13]([O:15][CH3:16])=[O:14])=O)[CH2:7][CH2:6][CH:5]=[CH:4][CH2:3]1.P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH3:18][C:17]1[O:19][C:8]([C:2]2([CH3:1])[CH2:7][CH2:6][CH:5]=[CH:4][CH2:3]2)=[N:10][C:11]=1[CH2:12][C:13]([O:15][CH3:16])=[O:14]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 13657847HCID 13657847, compound

Product 1

HCID 13282959HCID 13282959, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl 3-(1-methyl-3-cyclohexen-1-ylcarbonylamino)-4-oxovalerate (3.4 g), toluene (50 ml) and phosphorus oxychloride (3.5 ml) was refluxed for 3 hours and the solvent was distilled off. Aqueous sodium hydrogen carbonate was added, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off and the oily residue was further distilled under reduced pressure to give methyl 5-methyl-2-(1-methyl-3-cyclohexen-1-yl)-4-oxazoleacetate as an oil; yield 2.5 g (78.1%). Bp 120°-123° C. (0.3 mmHg).

Workup

  1. temperaturewas refluxed for 3 hours
  2. distillationthe solvent was distilled off
  3. additionAqueous sodium hydrogen carbonate was added
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off
  8. distillationthe oily residue was further distilled under reduced pressure

Sources & evidence

ORD record
ord-793d15699c3046fdb718edf6846fc17b
Source dataset
uspto-grants-1986_07
Patent number
US04602027

Reaction notes

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