Nitrogen → 1-(2-((2-Methoxyethoxy)methoxy)ethoxy)-4-nitrobenzene

HRID 2274293노트

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HRID 2274293 반응식
N#N.[N+:3]([C:6]1[CH:15]=[CH:14][C:9]([O:10][CH2:11][CH2:12][OH:13])=[CH:8][CH:7]=1)([O-:5])=[O:4].CCN(C(C)C)C(C)C.[CH3:25][O:26][CH2:27][CH2:28][O:29][CH2:30]Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl.O.C(OCC)(=O)C.CCCCCC>[CH3:25][O:26][CH2:27][CH2:28][O:29][CH2:30][O:13][CH2:12][CH2:11][O:10][C:9]1[CH:14]=[CH:15][C:6]([N+:3]([O-:5])=[O:4])=[CH:7][CH:8]=1

참가 물질

9

반응물 5

HCID 947NitrogenHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531DiisopropylethylamineHCID 853812-(4-Nitrophenoxy)ethanolHCID 516892Sodium Bicarbonate

생성물 1

HCID 902338741-(2-((2-Methoxyethoxy)methoxy)ethoxy)-4-nitrobenzene수율 65.9%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 21226206Ethyl acetate hexane용매

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온도
0 °C

실험 절차

Into a 100 mL 3-neck RBF, equipped with N2 Bubbler and thermo pocket 2-(4-nitrophenoxy)ethanol (10.8 g) in DCM (30 mL), and DIPEA (11.44 g) were added; the reaction mixture was cooled to 0° C. Methoxyethoxymethyl chloride (11.02 g in 20 mL DCM) was added drop wise during 10 min, and the reaction mixture was stirred at room temperature for 16 hr. The reaction was monitored on TLC using ethyl acetate:hexane (5:5) as mobile phase. After completion of the reaction, reaction mixture was poured into water and neutralized with saturated NaHCO3 solution. Product was extracted into DCM. The organic layer was washed with brine, dried over sodium sulfate and concentrated completely under reduce pressure at 40° C. to give 10.54 g of 1-(2-((2-methoxyethoxy)methoxy)ethoxy)-4-nitrobenzene.

후처리

  1. customAfter completion of the reaction, reaction mixture
  2. extractionProduct was extracted into DCM
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated completely
  6. customat 40° C.

출처 및 근거

ORD 기록
ord-a2c1a92c267940abaee67615eb066871
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126950B2

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