Diethyl Ether → 1-[2-(4-Phenoxyphenoxy)ethyl]pyrrolidine

HRID 1081388

反応式

HRID 1081388 の反応式
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.Cl[CH2:17][CH2:18][N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1.C([O-])([O-])=O.[K+].[K+].CCOCC>CN(C=O)C.O>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:17][CH2:18][N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 132544-PhenoxyphenolHCID 816681-(2-Chloroethyl)pyrrolidine hydrochloride

生成物 1

HCID 99939781-[2-(4-Phenoxyphenoxy)ethyl]pyrrolidine収率 92.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of 4-phenoxyphenol (0.56 g, 3.0 mmol), 1-(2-chloroethyl)-pyrrolidine HCl (0.51 g, 3.0 mmol) and powdered K2CO3 (1.2 g, 8.7 mmol) in 30 mL DMF was stirred at 80°-90° C. for 15 hours. The solution was cooled, poured into Et2O and water and the ether layer washed with water and brine, dried over Na2SO4 and concentrated in vacuo to give 0.79 g of a brown oil. The crude product was flashed chromatographed on silica gel using a gradient of 2:1 hexane/EtOAc to 100% EtOAc to provide the title compound (0.65 g, 76.5%) as a light yellow oil:

後処理

  1. temperatureThe solution was cooled
  2. washthe ether layer washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-caf2de2a0d274b8bb0ed5dee1174ec42
出典データセット
uspto-grants-1996_12
特許番号
US05585492

関連ノート

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