Azobisisobutyronitrile → Ethyl maleimide t-butyl 5-norbornene-2-carboxylate 3-hydroxypropyl bicyclo[2,2,2]oct-5-ene-2-carboxylate

HRID 1975893Notes

Reaction equation

HRID 1975893 reaction equation
[CH2:1]([C:3]1[C:4]([NH:6][C:7](=[O:9])[CH:8]=1)=[O:5])[CH3:2].[CH:10]12[CH2:16][CH:13]([CH:14]=[CH:15]1)[CH2:12][CH:11]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].[CH:24]12[CH2:31][CH2:30][CH:27]([CH:28]=[CH:29]1)[CH2:26][CH:25]2[C:32]([O:34][CH2:35][CH2:36]O)=[O:33].N(C(C)(C)C#N)=NC(C)(C)C#N>O1CCCC1>[CH2:1]([C:3]1[C:4]([NH:6][C:7](=[O:9])[CH:8]=1)=[O:5])[CH3:2].[CH:10]12[CH2:16][CH:13]([CH:14]=[CH:15]1)[CH2:12][CH:11]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].[CH:24]12[CH2:31][CH2:30][CH:27]([CH:28]=[CH:29]1)[CH2:26][CH:25]2[C:32]([O:34][CH2:35][CH2:36][CH2:4][OH:5])=[O:33]

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 14671028Ethyl maleimideHCID 15607334Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 1,1-dimethylethyl esterHCID 184136662-Hydroxyethyl bicyclo[2,2,2]oct-5-ene-2-carboxylate

Product 1

HCID 86756651Ethyl maleimide t-butyl 5-norbornene-2-carboxylate 3-hydroxypropyl bicyclo[2,2,2]oct-5-ene-2-carboxylateYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl maleimide (1 mol.), t-butyl 5-norbornene-2-carboxylate (0.5 mol.) and 2-hydroxyethyl bicyclo[2,2,2]oct-5-ene-2-carboxylate (0.5 mol) were dissolved in 50 g to 300 g of tetrahydrofuran (THF), 2 g to 15 g of 2,2′-azobisisobutyronitrile (AIBN) was added thereto, and the resulting solution was reacted at a temperature between 60° C. and 70° C. in a nitrogen atmosphere for 10 hours. After a high molecular weight was achieved by the reaction, the resultant product was precipitated in an ethyl ether or hexane solvent. The gathered precipitate was dried, and the desired poly(ethyl maleimide/t-butyl 5-norbornene-2-carboxylate/3-hydroxypropyl bicyclo[2,2,2]oct-5-ene-2-carboxylate) polymer was obtained at a yield of about 78%.

Workup

  1. customthe resulting solution was reacted at a temperature between 60° C. and 70° C. in a nitrogen atmosphere for 10 hours
  2. customAfter a high molecular weight was achieved by the reaction
  3. customthe resultant product was precipitated in an ethyl ether or hexane solvent
  4. customThe gathered precipitate was dried
  5. customwas obtained at a yield of about 78%

Sources & evidence

ORD record
ord-50827c55e9134e25a4a0dcf361e3b955
Source dataset
uspto-grants-2001_05
Patent number
US06225020B1

Reaction notes

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