Potassium Carbonate → 1-Methylanthracene

HRID 353317

反応式

HRID 353317 の反応式
OC[C:3]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](CNC)=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[CH:8]2.[C:20]([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:20][C:11]1[C:16]2[C:15](=[CH:10][C:9]3[C:4]([CH:3]=2)=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:14]=[CH:13][CH:12]=1

参加物

4

反応物 2

HCID 11430Potassium CarbonateHCID 22353076(10-Methylaminomethyl-anthracen-9-yl)-methanol

生成物 1

HCID 118841-Methylanthracene収率 103.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

10-(hydroxymethyl)-9-((methylamino)methyl)anthracene (0.800 g, 3.18 mmol) and K2CO3 (0.56 g, 4.05 mmol) were taken up in 15 mL acetonitrile. A solution of 2,2-dimethylpropane-1,3-diyl(o-(bromomethyl)phenyl)boronate 3 (1.00 g, 3.44 mmol) in 5 mL acetonitrile was added and the mixture was refluxed under nitrogen for 24 h. The mixture was filtered hot on a sintered-glass frit and upon cooling, a yellow solid precipitated. The resulting solid was triturated with acetonitrile/water (4:1, v/v), filtered on a sintered-glass frit and vacuum dried to yield 11 as a bright yellow solid (0.632 g, 51.6% yield): 1H NMR (300.13 MHz, CD3OD) δ2.58 (s, 3H), 4.58 (s, 2H), 5.22 (s, 2H), 5.61 (s, 2H), 7.62 (m, 6H), 7.80 (m, 2H), 8.18 (m, 2H), 8.58 (m, 2H); 13C-{1H} NMR (75.4 MHz, CD3OD) δ136.9, 136.2, 135.9, 132.9, 132.7, 131.4, 129.9, 128.3, 127.1, 126.8, 126.5, 124.9, 124.1, 63.8, 57.1, 50.9, 40.7.

後処理

  1. temperaturethe mixture was refluxed under nitrogen for 24 h
  2. filtrationThe mixture was filtered hot on a sintered-glass frit
  3. temperatureupon cooling
  4. customa yellow solid precipitated
  5. customThe resulting solid was triturated with acetonitrile/water (4:1
  6. filtrationv/v), filtered on a sintered-glass frit and vacuum
  7. customdried

出典と根拠

ORDレコード
ord-7d39d19b41bc4be28da0de1aa0b4cebb
出典データセット
uspto-grants-2004_06
特許番号
US06750311B1

関連ノート

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