4-Nitrophenol → 1-{2-[2-(2-Methoxyethoxy)ethoxy]ethoxy}-4-nitrobenzene

HRID 78705

反応式

HRID 78705 の反応式
CC1C=CC(S(O[CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+].[N+:28]([C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=1)([O-:30])=[O:29]>CN(C=O)C.O>[CH3:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:37][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 3

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

生成物 1

HCID 146918221-{2-[2-(2-Methoxyethoxy)ethoxy]ethoxy}-4-nitrobenzene収率 94.7%

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

To a stirred solution of 16 (1.83 g, 5.75 mmol) in anhydrous DMF (10 mL) were added K2CO3 (2.39 g, 17.3 mmol) and 4-nitrophenol (0.78 g, 5.59 mmol), and the reaction mixture was heated to 80° C. for 16 h. After cooling, the mixture was diluted in water, extracted three times with DCM, and then dried over MgSO4. The filtrate was concentrated under reduced pressure to give an oily residue, which was purified by flash chromatography over silica gel with Hex/EtOAc (1:2) to afford 17 as a yellow oil (1.51 g, 92%): 1H NMR (500 MHz, CDCl3) δ 8.19 (d, J=9.1 Hz, 2H), 6.97 (d, J=9.1 Hz, 2H), 4.26-3.65 (m, 12H), 3.37 (s, 3H).

後処理

  1. temperatureAfter cooling
  2. extractionextracted three times with DCM
  3. dry with materialdried over MgSO4
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto give an oily residue, which
  6. customwas purified by flash chromatography over silica gel with Hex/EtOAc (1:2)

出典と根拠

ORDレコード
ord-2394a121b57540eea619009698c28bfe
出典データセット
uspto-grants-2014_09
特許番号
US08841460B2

関連ノート

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