Toluene → 5-Norbornene 2-allylacetate 5-butylnorbornene 5-norbornene-2-carboxylic methylester

HRID 1160024ノート

反応式

HRID 1160024 の反応式
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH2:2]2.[CH2:8]([CH2:11][C:12]([O-:14])=[O:13])[CH:9]=[CH2:10].[CH2:15]([CH:19]1[CH2:24][CH:23]2[CH2:25][CH:20]1[CH:21]=[CH:22]2)[CH2:16][CH2:17][CH3:18].[CH3:26][O:27][C:28]([CH:30]1[CH2:35][CH:34]2[CH2:36][CH:31]1[CH:32]=[CH:33]2)=[O:29].C1(C)C=CC=CC=1>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2].C(O)C>[CH:1]12[CH2:7][CH:4]([CH:3]=[CH:2]1)[CH2:5][CH2:6]2.[CH2:8]([CH2:11][C:12]([O-:14])=[O:13])[CH:9]=[CH2:10].[CH2:15]([CH:19]1[CH2:24][CH:23]2[CH2:25][CH:20]1[CH:21]=[CH:22]2)[CH2:16][CH2:17][CH3:18].[CH3:26][O:27][C:28]([CH:30]1[CH2:35][CH:34]2[CH2:36][CH:31]1[CH:32]=[CH:33]2)=[O:29]

参加物

8

反応物 4

HCID 1140Toluene2 回HCID 168020Bicyclo[2.2.1]hept-2-ene, 5-butyl-HCID 250075Methyl bicyclo[2.2.1]hept-5-ene-2-carboxylateHCID 865975875-Norbornene 2-allylacetate

生成物 1

HCID 866039015-Norbornene 2-allylacetate 5-butylnorbornene 5-norbornene-2-carboxylic methylester

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 702Ethanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
90 °C

実験手順

5-norbornene-2-allylacetate (5 mL, 30.9 mmol), 5-butylnorbornene (1.2 mL, 6.6 mmol), 5-norbornene-2-carboxylic methylester (1 mL, 6.6 mmol) and toluene (12.4 mL) were charged into a 250 mL Schlenk flask. Pd(OAc)2 (0.66 mg, 2.94 μmol) and [(Cy)3PH][(B(C6F5)4) (5.65 mg, 5.88 μmol) were dissolved in CH2Cl2 (1 mL) and added to the monomer solution. While the reaction mixture was stirred for 18 hours at 90° C., the reaction mixture became viscous. After the reaction was completed, 120 ml of toluene was added to the viscous solution to dilute it. The solution was poured into an excess of ethanol to precipitate a white polymer, which was filtered through a glass funnel, washed with ethanol, and dried in vacuo at 80° C. for 24 hours to yield 5-norbornene-2-allylacetate/5-butylnorbornene/5-norbornene-2-carboxylic methylester polymer (6.45 g: 90.5% by weight based on the total weight of used monomers). The weight average molecular weight (Mw) of the polymer was 211,891 and Mw/Mn was 2.67.

後処理

  1. additionadded to the monomer solution
  2. additionto dilute it
  3. customto precipitate a white polymer, which
  4. filtrationwas filtered through a glass funnel
  5. washwashed with ethanol
  6. customdried in vacuo at 80° C. for 24 hours

出典と根拠

ORDレコード
ord-73911c09baf34fb89d312d7a9b4426db
出典データセット
uspto-grants-2010_10
特許番号
US07814713B2

反応ノート

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