5-Norbornene-2-carboxylic acid → HCID 86756135, compound

HRID 1276023

Reaction equation

HRID 1276023 reaction equation
[C:1]1(=[O:10])[N:5]([CH2:6][CH2:7][OH:8])[C:4](=[O:9])[CH:3]=[CH:2]1.[CH:11]12[CH2:17][CH:14]([CH:15]=[CH:16]1)[CH2:13][CH:12]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].[CH:25]12[CH2:31][CH:28]([CH:29]=[CH:30]1)[CH2:27][CH:26]2[C:32]([O:34][CH2:35][CH2:36][OH:37])=[O:33].[CH:38]12[CH2:44][CH:41]([CH:42]=[CH:43]1)[CH2:40][CH:39]2[C:45]([OH:47])=[O:46]>C1COCC1>[C:4]1(=[O:9])[N:5]([CH2:6][CH2:7][OH:8])[C:1](=[O:10])[CH:2]=[CH:3]1.[CH:11]12[CH2:17][CH:14]([CH:15]=[CH:16]1)[CH2:13][CH:12]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].[OH:37][CH2:36][CH2:35][O:34][C:32]([CH:26]1[CH2:27][CH:28]2[CH2:31][CH:25]1[CH:30]=[CH:29]2)=[O:33].[CH:38]12[CH2:44][CH:41]([CH:42]=[CH:43]1)[CH2:40][CH:39]2[C:45]([OH:47])=[O:46]

Participants

6

Reactant 4

HCID 789495-Norbornene-2-carboxylic acidHCID 458487N-(2-Hydroxyethyl)maleimideHCID 120338232-Hydroxyethyl bicyclo[2.2.1]hept-5-ene-2-carboxylateHCID 15607334Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 1,1-dimethylethyl ester

Product 1

HCID 86756135HCID 86756135, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Maleimidylethanol (12) (0.5 to 1 mol), 0.1 to 1 mol of t-butyl 5-norbornene-2-carboxylate (19), 0.05 to 1 mol of 2-hydroxyethyl 5-norbornene-2-carboxylate (21), and 0.01 to 0.3 mol of 5-norbornene-2-carboxylic acid (20) were dissolved in 150 to 250 g of THF solvent to which was added 0.5 to 20 g of AIEN as a polymerization initiator. The reaction mixture was allowed to react at 60° C. to 75° C. for 4 to 24 hours under an argon atmosphere. The resulting crude resin was precipitated with ethyl ether and dried to obtain poly[2-maleimidylethanol/t-butyl 5-norbornene-2-carboxylate/2-hydroxyethyl-5-norbornene-2-carboxylate/5-norbornene-2-carboxylic acid] copolymer resin.

Workup

  1. additionwas added 0.5 to 20 g of AIEN as a polymerization initiator
  2. customto react at 60° C. to 75° C. for 4 to 24 hours under an argon atmosphere
  3. customThe resulting crude resin was precipitated with ethyl ether
  4. customdried

Sources & evidence

ORD record
ord-e3eb390cad094b8da4196b8d74847e25
Source dataset
uspto-grants-2000_12
Patent number
US06165672

Linked notes

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