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

HRID 78705

반응식

HRID 78705 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-2394a121b57540eea619009698c28bfe
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841460B2

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