碘化钠 → 1-[2-(3-Methyl-2-nitrophenoxy)-ethyl]-pyrrolidine

HRID 6949

反应方程式

HRID 6949 反应方程式
C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH3:9][C:10]1[C:11]([N+:17]([O-:19])=[O:18])=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=1.Cl.Cl[CH2:22][CH2:23][N:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1>>[CH3:9][C:10]1[C:11]([N+:17]([O-:19])=[O:18])=[C:12]([CH:13]=[CH:14][CH:15]=1)[O:16][CH2:22][CH2:23][N:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1

参与物

5

反应物 4

HCID 5238碘化钠HCID 11430碳酸钾2 次HCID 210263-甲基-2-硝基苯酚HCID 81668N-(2-氯乙基)吡咯烷盐酸盐2 次

产物 1

HCID 116012601-[2-(3-Methyl-2-nitrophenoxy)-ethyl]-pyrrolidine收率 69%

实验过程

Potassium carbonate (34.9 g., 252 mmol) and sodium iodide (1.0 g., 6.5 mmol) were added to a solution of 3-methyl-2-nitrophenol (10 g., 65.3 mmol). With stirring, 1-(2-chloroethyl)-pyrrolidine hydrochloride (16.65 g., 98 mmol) was added portion-wise to the solution. The reaction mixture was refluxed for 15 hours, at which time 1-(2-chloroethyl)-pyrrolidine hydrochloride (8.5 g., 50 mmol) and potassium carbonate (18 g., 130 mmol) were added. After an additional hour of reflux, the reaction mixture was allowed to cool to room temperature and was washed with sequentially with water (1×100 mL) and brine (1×100 mL.) The combined organic fractions spontaneously crystallized, and the solid was purified by flash chromatography (5% MeOH in CH2Cl2) to give 1-[2-(3-Methyl-2-nitrophenoxy)-ethyl]-pyrrolidine (10.291 g., 69%). MS: 251 (M+H)+

后处理

  1. additionwere added
  2. temperatureAfter an additional hour of reflux
  3. washwas washed with sequentially with water (1×100 mL) and brine (1×100 mL.) The combined organic fractions
  4. customspontaneously crystallized
  5. customthe solid was purified by flash chromatography (5% MeOH in CH2Cl2)

来源与证据

ORD记录
ord-053aef3bb4e14e958a06b1ca6a830675
来源数据集
uspto-grants-2006_08
专利号
US07084169B2

关联笔记

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