Azobisisobutyronitrile → Maleic anhydride mono-2-ethyl-2-(hydroxymethyl)butyl bicyclo-[2.2.1]hept-5-ene-2,3-dicarboxylate tert-butyl bicyclo-[2.2.1]hept-5-ene-2-carboxylate tetrafluoro ethylene

HRID 1935299Notes

Reaction equation

HRID 1935299 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[CH:8]12[CH2:14][CH:11]([CH:12]=[CH:13]1)[CH:10]([C:15]([O-:17])=[O:16])[CH:9]2[C:18]([O:20][CH2:21][C:22]([CH2:27][CH3:28])([CH2:25][OH:26])[CH2:23][CH3:24])=[O:19].[CH:29]12[CH2:35][CH:32]([CH:33]=[CH:34]1)[CH2:31][CH:30]2[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37].[F:43][C:44]([F:48])=[C:45]([F:47])[F:46].CC(N=NC(C#N)(C)C)(C#N)C>O1CCCC1>[C:4]1(=[O:5])[O:6][C:1](=[O:7])[CH:2]=[CH:3]1.[CH:8]12[CH2:14][CH:11]([CH:12]=[CH:13]1)[CH:10]([C:15]([O-:17])=[O:16])[CH:9]2[C:18]([O:20][CH2:21][C:22]([CH2:27][CH3:28])([CH2:25][OH:26])[CH2:23][CH3:24])=[O:19].[CH:29]12[CH2:35][CH:32]([CH:33]=[CH:34]1)[CH2:31][CH:30]2[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37].[F:43][C:44]([F:48])=[C:45]([F:47])[F:46]

Participants

7

Reactant 5

HCID 6547AzobisisobutyronitrileHCID 7923Maleic AnhydrideHCID 8301TetrafluoroethyleneHCID 15607334Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 1,1-dimethylethyl esterHCID 86757924Mono-2-ethyl-2-(hydroxymethyl)butyl bicyclo-[2.2.1]hept-5-ene-2,3-dicarboxylate

Product 1

HCID 86758072Maleic anhydride mono-2-ethyl-2-(hydroxymethyl)butyl bicyclo-[2.2.1]hept-5-ene-2,3-dicarboxylate tert-butyl bicyclo-[2.2.1]hept-5-ene-2-carboxylate tetrafluoro ethylene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tetrahydrofuran was added 1.0 mole of maleic anhydride, 0.1 mole of mono-2-ethyl-2-(hydroxymethyl)butyl bicyclo-[2.2.1]hept-5-ene-2,3-dicarboxylate, 0.8 mole of tert-butyl bicyclo-[2.2.1]hept-5-ene-2-carboxylate, 0.1 mole of tetrafluoro ethene, and 0.5 to 10 g of AIBN. The resulting mixture was heated to temperature in the range of from about 60 to about 70° C. for 4 to 24 hours under a nitrogen or argon atmosphere.

Workup

  1. temperatureThe resulting mixture was heated to temperature in the range of from about 60 to about 70° C. for 4 to 24 hours under a nitrogen

Sources & evidence

ORD record
ord-9732f2807a2f4627a78ef76a31e7e7a3
Source dataset
uspto-grants-2002_05
Patent number
US06387589B1

Reaction notes

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