Maleimide → 3a,4,7,7a-Tetrahydro-4-methoxy-4,7-ethano-1H-isoindole-1,3(2H)-dione

HRID 1603687Notes

Reaction equation

HRID 1603687 reaction equation
[CH3:1][O:2][C:3]1[CH2:8][CH:7]=[CH:6][CH2:5][CH:4]=1.[C:9]1(=[O:15])[NH:13][C:12](=[O:14])[CH:11]=[CH:10]1>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]12[CH2:8][CH2:7][CH:6]([CH:5]=[CH:4]1)[CH:11]1[CH:10]2[C:9](=[O:15])[NH:13][C:12]1=[O:14]

Participants

4

Reactant 2

HCID 10935MaleimideHCID 761561-Methoxycyclohexa-1,4-diene

Product 1

HCID 152891533a,4,7,7a-Tetrahydro-4-methoxy-4,7-ethano-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

11 g (0.1 mol) of 1-methoxycyclohexa-1,4-diene are heated under reflux with 0.1 g of tris(triphenylphosphine)-ruthenium dichloride and 8.8 g (0.09 mol) of maleimide in 100 ml of absolute chloroform overnight. The mixture is concentrated and the residue is recrystallized from 100 ml of toluene.

Workup

  1. concentrationThe mixture is concentrated
  2. customthe residue is recrystallized from 100 ml of toluene

Sources & evidence

ORD record
ord-a9ac828e9f3e45029e72cdc9ecb9dc02
Source dataset
uspto-grants-1999_11
Patent number
US05990122

Reaction notes

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