2-Methoxyethanol → 2-(Benzyloxy)-1-(2-methoxyethoxy)-4-nitrobenzene

HRID 2274262노트

반응식

HRID 2274262 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1F)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][O:20][CH2:21][CH2:22][OH:23].C([O-])([O-])=O.[Cs+].[Cs+].CCCCCC.C(OCC)(=O)C>O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[O:23][CH2:22][CH2:21][O:20][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 80192-MethoxyethanolHCID 10796Cesium carbonateHCID 21226206Ethyl acetate hexaneHCID 694127502-(Benzyloxy)-1-fluoro-4-nitrobenzene

생성물 1

HCID 867243352-(Benzyloxy)-1-(2-methoxyethoxy)-4-nitrobenzene

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

Into a 25 mL 3-neck RBF equipped with reflux condenser and thermo pocket were charged 2-(benzyloxy)-1-fluoro-4-nitrobenzene (3.3 g), 2-methoxy ethanol (16.0 mL) and Cs2CO3 (8.67 g). The reaction mixture was heated at 80° C. for 2 hr. The reaction was monitored on TLC using hexane:ethyl acetate (5:5) as mobile phase. The reaction was complete after 2 hr. After completion, the reaction mixture was cooled to room temperature and poured into cold water. Solid precipitate was filtered and washed with water. Solid was dried under reduced pressure. The obtained 3.90 g of solid 2-(benzyloxy)-1-(2-methoxyethoxy)-4-nitrobenzene was taken onto the next step without further purification. 1H NMR: DMSO-d6 (400 MHz): 3.34 (s, 3H), 3.722-3.700 (t, 2H, J=4.4), 4.269-4.291 (t, 2H, J=4.4), 5.256 (s, 2H), 7.216-7.239 (d, 1H, J=9.2), 7.328-7.364 (m, 1H), 7.393-7.430 (m, 2H), 7.471 (s, 1H), 7.489 (s, 1H), 7.849-7.855 (d, 1H, J=2.4), 7.889-7.971 (dd, 1H, J=2.4, 6.4).

후처리

  1. customInto a 25 mL 3-neck RBF equipped
  2. temperaturewith reflux condenser
  3. temperatureAfter completion, the reaction mixture was cooled to room temperature
  4. filtrationSolid precipitate was filtered
  5. washwashed with water
  6. customSolid was dried under reduced pressure
  7. customThe obtained 3.90 g of solid 2-(benzyloxy)-1-(2-methoxyethoxy)-4-nitrobenzene was taken onto the next step without further purification

출처 및 근거

ORD 기록
ord-6269ef5f72ae47dbb909813b7e03eb89
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126950B2

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