Methyl Acrylate → 4,5-Dihydro-5-(methoxycarbonyl)-3-isoxazolepropanoic acid methyl ester

HRID 653418Notes

Reaction equation

HRID 653418 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH2:4][CH2:5][CH2:6][N+:7]([O-:9])=O.[C:11]([O:15][CH3:16])(=[O:14])[CH:12]=[CH2:13].C(N(CC)CC)C.C1(N=C=O)C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:16][O:15][C:11](=[O:14])[CH2:12][CH2:13][C:6]1[CH2:5][CH:4]([C:3]([O:2][CH3:1])=[O:10])[O:9][N:7]=1

Participants

6

Reactant 4

HCID 7294Methyl AcrylateHCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 25604Methyl 4-nitrobutyrate

Product 1

HCID 139115534,5-Dihydro-5-(methoxycarbonyl)-3-isoxazolepropanoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 23.8 g of 4-nitrobutyric acid methyl ester (made in accordance with Bruson, U.S. Pat. No. 2,342,119) 39.6 g of methyl acrylate, 0.2 g triethyl amine in 200 ml of toluene is stirred and treated dropwise with 23.8 g of phenyl isocyanate. The mixture is stirred for 72 hours at room temperature and heated at 90° C. for two hours. The mixture is cooled, filtered to remove the diphyl urea, and concentrated under reduced pressure. The resulting oil is chromatographed on SiO2 (elution with hexane:ethyl-acetate; 75:25) to yield 4,5-dihydro-5-(methoxycarbonyl)-3-isoxazolepropanoic acid methyl ester as a colorless oil. NMR (CDCl3) and 4.93 (t, J=9 Hz, 1H), 3.72 (s, 3H), 3.63 (s, 3H), 3.20 (d, J-9 Hz, 2H), 2.61 (s, 4H). IR (KBr) 2956, 2851, 1739, 1632, 1439, 1367, 1340, 1215. IR (cm-1).

Workup

  1. temperatureheated at 90° C. for two hours
  2. temperatureThe mixture is cooled
  3. filtrationfiltered
  4. customto remove the diphyl urea
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting oil is chromatographed on SiO2 (elution with hexane:ethyl-acetate; 75:25)

Sources & evidence

ORD record
ord-0f72895e226444d39f2c42e5cf2750a1
Source dataset
uspto-grants-1987_06
Patent number
US04677114

Reaction notes

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