HCID 131722517, compound → 2-Methyl-5-(2-(3-methylphenyl)ethyl)-4-oxazole carboxylic acid, ethyl ester

HRID 324426Notes

Reaction equation

HRID 324426 reaction equation
[C:1]([NH:4][CH:5]([C:11](=[O:21])[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=O)[CH3:2]>S(Cl)(Cl)=O>[CH3:2][C:1]1[O:21][C:11]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=2)=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[N:4]=1

Participants

3

Reactant 1

HCID 131722517HCID 131722517, compound

Product 1

HCID 1317225182-Methyl-5-(2-(3-methylphenyl)ethyl)-4-oxazole carboxylic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent2×

Procedure

Thionyl chloride (200 ml) was added dropwise over 15 min to the product from step (ii) (70 g) with cooling provided by an ice bath. The mixture was then set at reflux for 1 h. After cooling to room temperature the thionyl chloride was evaporated under reduced pressure and the residue partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic layer was collected, dried over magnesium sulphate and solvent removed under reduced pressure. Purification of the residue was performed by flash chromatography eluting with 2% ethanol in dichloromethane.

Workup

  1. temperaturewith cooling
  2. customprovided by an ice bath
  3. temperatureat reflux for 1 h
  4. customwas evaporated under reduced pressure
  5. customthe residue partitioned between ethyl acetate and saturated sodium bicarbonate solution
  6. customThe organic layer was collected
  7. dry with materialdried over magnesium sulphate and solvent
  8. customremoved under reduced pressure
  9. customPurification of the residue
  10. washeluting with 2% ethanol in dichloromethane

Sources & evidence

ORD record
ord-8215fe167e4d4601ba3ba1ee972468c4
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

Loading…