2,2'-Bipyridine → 3-[1-(3-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]phenol

HRID 340853

反応式

HRID 340853 の反応式
C[Si](C)(C)[C:3]#[C:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1.[N:14]([C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1)=[N+:15]=[N-:16].N1C=CC=CC=1C1C=CC=CN=1>CN(C=O)C.CCOC(C)=O>[OH:23][C:19]1[CH:18]=[C:17]([N:14]2[CH:3]=[C:4]([C:5]3[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=3)[N:16]=[N:15]2)[CH:22]=[CH:21][CH:20]=1

参加物

6

反応物 3

HCID 14742,2'-BipyridineHCID 113670133-AzidophenolHCID 220877193-((Trimethylsilyl)ethynyl)phenol

生成物 1

HCID 167211153-[1-(3-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]phenol収率 70%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To 3-TMSE-phenol (4.0 g, 21.02 mmol) in 35 mL of DMF were added 3-azidophenol (3.41 g, 25.2 mmol), CuBr (153 mg, 1.05 mmol), and 2,2′-bipyridyl (328 mg, 2.10 mmol). The mixture was heated at 80° C. for 24 h, cooled to room temperature, then diluted with 250 mL of EtOAc. The combined organic mixture washed with water, and dried over MgSO4. Solvents were removed by rotary evaporation, and the residue was recrystallized in acetic acid/water to give 3.70 g (70% yield) of a brown crystalline solid. 1H NMR (MeOD-d4, 300 MHz, ppm): 8.80 (s, 1H, triazol-H), 7.43-7.26 (m, 6H, Ar—H), 6.95-6.91 (m, 1H, Ar—H), 6.84-6.83 (m, 1H, Ar—H). 13C NMR (MeOD-d4, 75 MHz, ppm): 158.6, 157.7, 148.1, 137.9, 131.1, 130.4, 129.7, 118.8, 116.7, 115.6, 115.1, 112.1, 110.7, 107.1.

後処理

  1. temperaturecooled to room temperature
  2. washThe combined organic mixture washed with water
  3. dry with materialdried over MgSO4
  4. customSolvents were removed by rotary evaporation
  5. customthe residue was recrystallized in acetic acid/water

出典と根拠

ORDレコード
ord-80c982d2787b48b6a578d815f090cc87
出典データセット
uspto-grants-2014_11
特許番号
US08895688B2

関連ノート

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