Methyl Acrylate → HCID 13921017, compound

HRID 653399Notes

Reaction equation

HRID 653399 reaction equation
[C:1]([O:5][C:6](=[O:13])[CH2:7][CH2:8][CH2:9][N+:10]([O-:12])=O)([CH3:4])([CH3:3])[CH3:2].[C:14]([O:18][CH3:19])(=[O:17])[CH:15]=[CH2:16].C(N(CC)CC)C.C1(N=C=O)C=CC=CC=1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:13])[CH2:7][CH2:8][C:9]1[CH2:16][CH:15]([C:14]([O:18][CH3:19])=[O:17])[O:12][N:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 7294Methyl AcrylateHCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 13921016HCID 13921016, compound

Product 1

HCID 13921017HCID 13921017, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 18.9 g of 4-nitrobutyric acid t-butyl ester, 8.6 g of methyl acrylate, 0.2 g triethyl amine in 200 ml of toluene is stirred and treated dropwise with 27.4 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 diphenyl urea, and concentrated under reduced pressure. The resulting oil is chromatographed on SiO2 (elution with hexane:ethylacetate; 75:25) to yield 4,5-dihydro-5-(methoxycarbonyl)-3-isoxazolepropanoic acid t-butyl ester as a colorless oil. NMR (CDCl3) and 5.00 (t, J=9 Hz, 1H), 3.77 (s, 3HO, 3.28 (d, J=9 Hz, 2H), 2.58 (s, 4H), 1.42 (s, 9H). IR (cm-1) 2955, 2910, 1728, 1545, 1437, 1385, 1370, 1340, 12155, 1215.

Workup

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

Sources & evidence

ORD record
ord-57f76d4c1e1c49a5bb4b385c5417fd05
Source dataset
uspto-grants-1987_06
Patent number
US04677098

Reaction notes

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