Methyl Acrylate → Methyl 3-[2-oxo-4-(4-trifluoromethylphenyl)-4-oxazolin-5-yl]propionate

HRID 563113Notes

Reaction equation

HRID 563113 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][C:11](=[O:14])[O:12][CH:13]=2)=[CH:5][CH:4]=1.[C:17]([O:21][CH3:22])(=[O:20])[CH:18]=[CH2:19]>C1(C)C=CC=CC=1>[O:14]=[C:11]1[NH:10][C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:15])[F:16])=[CH:8][CH:7]=2)=[C:13]([CH2:19][CH2:18][C:17]([O:21][CH3:22])=[O:20])[O:12]1

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 129929584-(4-Trifluoromethylphenyl)-2-oxazolone

Product 1

HCID 23431800Methyl 3-[2-oxo-4-(4-trifluoromethylphenyl)-4-oxazolin-5-yl]propionateYield 27%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-(4-trifluoromethylphenyl)-2-oxazolone (10.8 g), methyl acrylate (8.10 g), boron trifluoride diethyl ether complex (6.86 g) and toluene (50 ml) was stirred with heating under reflux for 3 hours. The reaction mixture was concentrated, and poured into ice water (200 ml). The solid precipitates were filtered, washed with water, and air-dried. Recrystallization from isopropyl alcohol-isopropyl ether gave methyl 3-[2-oxo-4-(4-trifluoromethylphenyl)-4-oxazolin-5-yl]propionate as pale yellow prisms (4.00 g, 27%). Melting point 156-157° C.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated
  4. additionpoured into ice water (200 ml)
  5. customThe solid precipitates
  6. filtrationwere filtered
  7. washwashed with water
  8. customair-dried
  9. customRecrystallization from isopropyl alcohol-isopropyl ether

Sources & evidence

ORD record
ord-44ee85af28814762b5391fb0e7f88181
Source dataset
uspto-grants-2011_11
Patent number
US08067453B2

Reaction notes

Loading…