Sodium Iodide → 1-[2-(3-Methyl-2-nitrophenoxy)-ethyl]-pyrrolidine

HRID 6949

反応式

HRID 6949 の反応式
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

参加物

5

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium Carbonate2 回HCID 210263-Methyl-2-nitrophenolHCID 816681-(2-Chloroethyl)pyrrolidine hydrochloride2 回

生成物 1

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

実験手順

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)+

後処理

  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)

出典と根拠

ORDレコード
ord-053aef3bb4e14e958a06b1ca6a830675
出典データセット
uspto-grants-2006_08
特許番号
US07084169B2

関連ノート

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