1-Bromo-2,4-dimethoxybenzene → HCID 44610346、化合物

HRID 1966012ノート

反応式

HRID 1966012 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1Br.C([Li])CCC.[I-].[CH3:18][N+:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1>C(OCC)C.O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:24]1[CH:23]=[C:22]([CH3:25])[CH:21]=[CH:20][N:19]1[CH3:18]

参加物

6

反応物 3

HCID 872661-Bromo-2,4-dimethoxybenzeneHCID 2006031,4-Dimethylpyridinium IodideHCID 178418339Butyllithium

生成物 1

HCID 44610346HCID 44610346、化合物収率 93%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
-78 °C

実験手順

To a stirred solution of 2,4-dimethoxybromobenzene (1) (0.5 g, 2.3 mmol) in diethyl ether (10 ml) cooled at −78° C. under nitrogen was added a solution of n-butyl lithium (1.0 ml, 2.5 mmol of 2.5M solution in hexane) drop wise. The mixture was stirred at −78° C. for 2 hours and then 1,4-dimethylpyridinium iodide (2) (0.54 g, 2.5 mmol) was added as a solid. The resultant mixture was allowed to warm to room temperature and stirred at room temperature for 18 hours. The mixture was diluted with water (20 ml) and extracted with diethyl ether (2×15 ml). The combined organic extracts were dried over anhydrous magnesium sulphate, filtered and evaporated to yield 2-(2,4-dimethoxyphenyl)-1,4-dimethyl-1,2-dihydropyridine (4) (0.5 g, 93%) as a brown oil, 1H NMR CDCl3 ?? 1.7 (s, 3H), 2.7 (s, 3H), 3.8 (s, 6H), 4.45 (dd, 1H, J=2.7) 4.85 (m, 1H), 5.4 (d, 1H, J=4), 6.05 (d, 1H, J=7), 6.45 (d, 1H, J=3), 6.55 (m, 1H), 7.5 (d, 1H, J=9).

後処理

  1. temperatureto warm to room temperature
  2. stirringstirred at room temperature for 18 hours
  3. extractionextracted with diethyl ether (2×15 ml)
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-463540c75e9646aca2673da579d6ffea
出典データセット
uspto-grants-2013_04
特許番号
US08420637B2

反応ノート

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