Hydrochloric Acid → 6-(4-Methoxy-2-nitrophenoxy)-2-phenylchroman

HRID 31168

反応式

HRID 31168 の反応式
[C:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([OH:17])[CH:13]=3)[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=1[N+:27]([O-:29])=[O:28].[OH-].[K+].[I-].[K+].Cl>CS(C)=O>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([O:17][C:12]2[CH:13]=[C:14]3[C:9](=[CH:10][CH:11]=2)[O:8][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:16][CH2:15]3)=[C:20]([N+:27]([O-:29])=[O:28])[CH:21]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 14797Potassium HydroxideHCID 251404-Chloro-3-nitroanisoleHCID 212875382-Phenylchroman-6-ol

生成物 1

HCID 179785656-(4-Methoxy-2-nitrophenoxy)-2-phenylchroman

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
90 °C

実験手順

The 2-phenylchroman-6-ol (500 mg) and 1-chloro-4-methoxy-2-nitrobenzene (390 mg) were dissolved in DMSO (10 ml). Potassium hydroxide (230 mg) and potassium iodide (520 mg) were added and the resulting mixture was stirred at 90° C. for 1 hour. After cooling it was poured in to 1 M HCl-solution (20 ml) and extracted with dichloromethane. The combined organic layers were washed with water until neutral and then with saturated NaCl-solution and dried with Na2SO4. After evaporating the solvents the 6-(4-Methoxy-2-nitrophenoxy)-2-phenylchroman was obtained by trituration with methanol. 1H NMR (400 MHz, d6-DMSO) δ: 7.58 (d, 1H, J 3.1 Hz), 7.45-7.33 (m, 6H), 7.28 (dd, 1H, J 9.2 Hz, 3.1 Hz), 7.10 (d, 1H, J 9.2 Hz), 6.86-6.78 (m, 3H), 5.10 (dd, 1H, J 10.0, 1.9 Hz), 3.83 (s, 3H), 2.92 (ddd, 1H, J −16.9, 11.2, 5.9 Hz), 2.75 (ddd, 1H, J −16.9, 7.9, 4.2 Hz), 2.15 (m, 1H), 1.97 (m, 1H).

後処理

  1. temperatureAfter cooling it
  2. extractionextracted with dichloromethane
  3. washThe combined organic layers were washed with water until neutral and then with saturated NaCl-solution
  4. dry with materialdried with Na2SO4
  5. customAfter evaporating the solvents the 6-(4-Methoxy-2-nitrophenoxy)-2-phenylchroman
  6. customwas obtained by trituration with methanol

出典と根拠

ORDレコード
ord-f51f27b887bf448bae57e635add84780
出典データセット
uspto-grants-2008_09
特許番号
US07425568B2

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