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

HRID 1603211Notes

Reaction equation

HRID 1603211 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-b33e640e3e224240b94beeac44c51b09
Source dataset
uspto-grants-1999_11
Patent number
US05986105

Reaction notes

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