Cesium carbonate → 2-(2,2-Dimethyl-2,3-dihydrobenzofuran-7-yloxy)-3-nitropyridine

HRID 555408

反応式

HRID 555408 の反応式
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:11][C:12]1([CH3:22])[CH2:16][C:15]2[CH:17]=[CH:18][CH:19]=[C:20]([OH:21])[C:14]=2[O:13]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[CH3:11][C:12]1([CH3:22])[CH2:16][C:15]2[CH:17]=[CH:18][CH:19]=[C:20]([O:21][C:2]3[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=3)[C:14]=2[O:13]1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 152782,3-Dihydro-2,2-dimethyl-7-benzofuranolHCID 796132-Chloro-3-nitropyridine

生成物 1

HCID 39410562-(2,2-Dimethyl-2,3-dihydrobenzofuran-7-yloxy)-3-nitropyridine収率 73.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A solution of 2-chloro-3-nitropyridine (4.9 g, 30.9 mmol) in DMF (50 mL) was treated with 2,2-dimethyl-2,3-dihydrobenzofuran-7-ol (5.3 mL, 46.4 mmol) and cesium carbonate (30.2 g, 92.7 mmol). The mixture was heated at 80° C. for 10 h. The reaction was cooled to rt, and the mixture was poured in water (200 mL) with stirring. The yellow precipitate formed was filtered and washed with water, and recrystallized from ethanol (50 mL) to afford 134a as brown crystals (6.5 g, 73% yield). [M+H]+=287.16. 1H NMR (500 MHz, deuterochloroform) δ ppm 8.38 (dd, 1H, J=1.7 Hz, J=5.0 Hz), 8.31 (dd, 1H, J=5.0 Hz, J=1.7 Hz), 7.12 (dd, 1H, J=10.0 Hz, J=5.0 Hz), 7.05 (d, 1H, J=5.0 Hz), 7.00 (d, 1H, J=10.0 Hz), 6.86 (t, 1H, J=10.0 Hz), 3.05 (s, 2H), 1.39 (s, 6H); 13C (125 MHz, deuterochloroform) δ (ppm), 155.42, 151.76, 150.16, 136.03, 135.40, 134.04, 129.76, 122.60, 121.06, 120.37, 118.07, 88.40, 43.07, 27.98.

後処理

  1. temperatureThe reaction was cooled to rt
  2. customThe yellow precipitate formed
  3. filtrationwas filtered
  4. washwashed with water
  5. customrecrystallized from ethanol (50 mL)

出典と根拠

ORDレコード
ord-75954834955a447cae9e69555b38ac74
出典データセット
uspto-grants-2011_11
特許番号
US08053450B2

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