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

HRID 2274293ノート

反応式

HRID 2274293 の反応式
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

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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.

出典と根拠

ORDレコード
ord-a2c1a92c267940abaee67615eb066871
出典データセット
uspto-grants-2015_09
特許番号
US09126950B2

反応ノート

読み込み中…