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

HRID 555408

반응식

HRID 555408 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-75954834955a447cae9e69555b38ac74
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08053450B2

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