Water → HCID 66927727、化合物

HRID 131081

反応式

HRID 131081 の反応式
C1(C)C=CC(S(O[CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].[N+:28]([C:31]1[CH:36]=[CH:35][C:34](O)=[CH:33][CH:32]=1)([O-:30])=[O:29].O>CN(C)C=O>[CH3:20][O:19][CH2:18][CH2:17][O:16][CH2:15][CH2:14][O:13][CH2:12][CH2:11][C:34]1[CH:35]=[CH:36][C:31]([N+:28]([O-:30])=[O:29])=[CH:32][CH:33]=1

参加物

6

反応物 4

HCID 962WaterHCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 99488982-(2-(2-Methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate

生成物 1

HCID 66927727HCID 66927727、化合物収率 77.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A portion of 13 (9.0 g, 28.3 mmol) was dissolved in 50 mL of dimethylformamide. Potassium carbonate (11.75 g, 85.0 mmol) and 4-nitrophenol (3.82 g, 27.5 mmol) were added. The solution was stirred at 80° C. for 16 hours. After cooling to room temperature, the solution was poured into water and extracted three times with methylene chloride. The combined organic layers were washed with water, then brine, dried over magnesium sulfate, filtered, and the solvent was removed by distillation at reduced pressure. Chromatography (silica, hexane:ethyl acetate, 1:2) was employed to isolate the product (5.71 g, 73% yield). IR (neat) 3109.2, 3078.2, 2878.5, 1726.3, 1588.1, 1511.2, 1337.1, 1106.7, 1050.3, 932.6, 845.5, 753.3, 656.1 cm−1. 1H NMR (CDCl3) δ 8.07 (d, J=9.3 Hz, 2H), 6.88 (d, J=9.3 Hz, 2H), 4.12 (app t, 2H), 3.79 (app t, 2H), 3.62 (m, 2H), 3.58 to 3.53 (m, 4H), 3.44 to 3.42 (m, 2 H), 3.26 (s, 3 H); 13C NMR (100 MHz, CDCl3) δ 164.29, 141.93, 126.24, 114.99, 72.29, 71.29, 71.03, 70.98, 69.77, 68.60, 59.44.

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionextracted three times with methylene chloride
  3. washThe combined organic layers were washed with water
  4. dry with materialbrine, dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed by distillation at reduced pressure

出典と根拠

ORDレコード
ord-5e97ae47f478442a93f38cf080cab1a8
出典データセット
uspto-grants-2008_06
特許番号
US07384815B2

関連ノート

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