Methyl Acrylate → Methyl 2-(4-(4-chlorophenyl)-2-oxo-4-oxazolin-5-yl)propionate

HRID 47924Notes

Reaction equation

HRID 47924 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[O:13])[O:11][CH:12]=2)=[CH:4][CH:3]=1.[C:14]([O:18][CH3:19])(=[O:17])[CH:15]=[CH2:16].C(N(CC)CC)C>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:9][C:10](=[O:13])[O:11][C:12]=2[CH:15]([CH3:16])[C:14]([O:18][CH3:19])=[O:17])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 114241254-(4-Chlorophenyl)-2,3-dihydro-1,3-oxazol-2-one

Product 1

HCID 11150230Methyl 2-(4-(4-chlorophenyl)-2-oxo-4-oxazolin-5-yl)propionateYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

4-(4-Chlorophenyl)-2-oxo-4-oxazoline (3.0 g) was dissolved in methanol (30 mL) and methyl acrylate (1.66 mL) and triethylamine (2.14 mL) were added. The obtained mixture was stirred with reflux for 6 h, and the solvent was concentrated under reduced pressure. Isopropanol (9 mL) and isopropyl ether (21 mL) were added, and the mixture was allowed to stand at room temperature overnight and was cooled to not higher than 5° C. and stirred for 1 h. The precipitated crystals were collected by filtration and washed with isopropyl ether to give the title compound (2.81 g; yield 65.0%).

Workup

  1. temperaturewith reflux for 6 h
  2. concentrationthe solvent was concentrated under reduced pressure
  3. additionIsopropanol (9 mL) and isopropyl ether (21 mL) were added
  4. stirringstirred for 1 h
  5. filtrationThe precipitated crystals were collected by filtration
  6. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-f8d0ae6f6fd14175b7df246221d57654
Source dataset
uspto-grants-2004_03
Patent number
US06699995B1

Reaction notes

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