Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 1,1-dimethylethyl ester → HCID 131723175, compound

HRID 841002Notes

Reaction equation

HRID 841002 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[C:8]([O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)=[O:9].[CH:17]12[CH2:23][CH:20]([CH:21]=[CH:22]1)[CH2:19][CH:18]2[C:24]([O:26][C:27]([CH3:30])(C)C)=[O:25]>>[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[C:8]([O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)=[O:9].[CH:17]12[CH2:23][CH:20]([CH:21]=[CH:22]1)[CH2:19][CH:18]2[C:24]([O:26][CH2:27][CH2:30][OH:9])=[O:25].[CH3:11][O:10][C:8]([CH:2]1[CH:3]([C:24]([OH:26])=[O:25])[CH:4]2[CH:5]=[CH:6][CH:1]1[CH2:7]2)=[O:9].[C:8]1(=[O:9])[O:10][C:11](=[O:12])[CH:16]=[CH:15]1

Participants

3

Reactant 2

HCID 15607334Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 1,1-dimethylethyl esterHCID 21922341HCID 21922341, compound

Product 1

HCID 131723175HCID 131723175, compoundYield 68%

Procedure

The same procedure described in Example 1 was repeated but 2-tetrahydropyranyl 5-norbornene-2-carboxylate, prepared according to Preparation Example III was used instead of tert-butyl 5-norbornene-2 carboxylate, to obtain the title copolymer resin (formula V) having a molecular weight of 3,000-100,000 (yield: 68%). Though the protective group of the copolymer resin thus prepared was substituted by an acetal group, etching resistance of the resin did not deteriorate and the resin had excellent sensitivity (sensitivity: 11 Nj/cm2).

Workup

  1. customaccording to Preparation Example III

Sources & evidence

ORD record
ord-679a019975d64aa8a287364c3b72af51
Source dataset
uspto-grants-2002_04
Patent number
US06369181B1

Reaction notes

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