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

HRID 1482679ノート

反応式

HRID 1482679 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1c4842349e7b40a2b6ad6e20e32d9cce
出典データセット
uspto-grants-2016_08
特許番号
US09415049B2

反応ノート

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