Potassium Carbonate → 1-Methylanthracene

HRID 353317

반응식

HRID 353317 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 118841-Methylanthracene수율 103.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7d39d19b41bc4be28da0de1aa0b4cebb
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06750311B1

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