Furan → 4,7-Epoxy-1H-isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-

HRID 2382218Notes

Reaction equation

HRID 2382218 reaction equation
[C:1]1(=[O:7])[NH:5][C:4](=[O:6])[CH:3]=[CH:2]1.[O:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1>C(OCC)C>[O:8]1[CH:12]2[CH:11]=[CH:10][CH:9]1[CH:3]1[C:4](=[O:6])[NH:5][C:1](=[O:7])[CH:2]12

Participants

4

Reactant 2

HCID 8029FuranHCID 10935Maleimide

Product 1

HCID 960004,7-Epoxy-1H-isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-Yield 46.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of maleimide (Sigma-Aldrich, St. Louis Mo.; 2.0 g, 0.0206 moles) and furan (Sigma-Aldrich, St. Louis Mo.; 7.49 mL, 0.103 moles) in anhydrous ethyl ether (50 mL) was stirred for 70 hours at room temperature under an argon atmosphere. A white precipitate formed during the reaction and was filtered off and dried under reduced pressure giving 1.57 g of white crystals. NMR (d6-DMSO): Mixture of exo- and endo-isomers (37:63) of ETPI: Exo-3,6-Epoxy-1,2,3,6-tetrahydrophthalimide: 2.85 ppm (s, —CH, 2H), 5.25 ppm (s, —CH, 1H), 6.55 ppm (s, —CH═CH—, 2H), Endo-3,6-Epoxy-1,2,3,6-tetrahydrophthalimide: 3.48 ppm (s, —CH, 2H), 5.11 ppm (s, —CH, 2H), 6.49 ppm (s, —CH═CH, 2H).

Workup

  1. customA white precipitate formed during the reaction
  2. filtrationwas filtered off
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-b2fadbd5b9384dbc9ab00ec4b1679cae
Source dataset
uspto-grants-2012_09
Patent number
US08258324B2

Reaction notes

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