Methyl Acrylate → 2-Benzyl-3-phenyl-5-methoxycarbonylisoxazolidine

HRID 2248029

Reaction equation

HRID 2248029 reaction equation
[CH:1](=[N+:8]([O-:16])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O:21][CH3:22])(=[O:20])[CH:18]=[CH2:19].CCCCCCC.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:19][CH:18]([C:17]([O:21][CH3:22])=[O:20])[O:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7294Methyl AcrylateHCID 8857Ethyl AcetateHCID 8900HeptaneHCID 305634Benzenemethanamine,N-(phenylmethylene)-, N-oxide

Product 1

HCID 198163412-Benzyl-3-phenyl-5-methoxycarbonylisoxazolidineYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 8.0 g (37.9 mmol) of N-benzylidenebenzylamine N-oxide and 6.69 g (77.7 mmol) of methyl acrylate in 20 ml of toluene is heated under reflux for 12 hours. The reaction mixture is evaporated under reduced pressure to give a pale yellow oil. Flash chromatography (silica gel, 2:1 heptane:ethyl acetate) affords 8.0 g of the title compound as a pale yellow oil.

Workup

  1. temperatureunder reflux for 12 hours
  2. customThe reaction mixture is evaporated under reduced pressure
  3. customto give a pale yellow oil

Sources & evidence

ORD record
ord-c165dc18008b4ca0bc18226b11441584
Source dataset
uspto-grants-1991_08
Patent number
US05037867

Linked notes

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