Ethyl Acetate → 2-(2-{2-[4-(3-Methoxyphenyl)butyl]phenoxy}ethyl)-1-methylpyrrolidine

HRID 743324ノート

反応式

HRID 743324 の反応式
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[OH:25])[CH:12]=[CH:13][CH:14]=1.Cl.Cl[CH2:28][CH2:29][CH:30]1[CH2:34][CH2:33][CH2:32][N:31]1[CH3:35].C(OCC)(=O)C>CC(N(C)C)=O.O>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH2:28][CH2:29][CH:30]2[CH2:34][CH2:33][CH2:32][N:31]2[CH3:35])[CH:12]=[CH:13][CH:14]=1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 3017050Pyrrolidine, 2-(2-chloroethyl)-1-methyl-, hydrochloride (1:1)HCID 108010802-[4-(3-Methoxyphenyl)butyl]phenolHCID 23665647Potassium tert-butoxide

生成物 1

HCID 105252452-(2-{2-[4-(3-Methoxyphenyl)butyl]phenoxy}ethyl)-1-methylpyrrolidine収率 48%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 31374Dimethylacetamide溶媒

実験手順

1.48 g of potassium t-butoxide were added to a solution of 1.35 g of 2-[4-(3-methoxyphenyl)butyl]phenol (prepared as described in Preparation 7) in 20 ml of dimethylacetamide, whilst ice-cooling and stirring. 1.45 g of 2-(2-chloroethyl)-1-methylpyrrolidine hydrochoride were then added to the solution, and the mixture was stirred at 55° C. for 2 hours. At the end of this time, the reaction mixture was cooled, 200 ml of ethyl acetate and 100 ml of water were added to the mixture, and the mixture was shaken. The ethyl acetate layer was separated, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The ethyl acetate layer was then concentrated by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 10:1 by volume mixture of methylene chloride and methanol as the eluent, to give 0.92 g (yield 48%) of the title compound as an oil.

後処理

  1. temperaturecooling
  2. stirringthe mixture was stirred at 55° C. for 2 hours
  3. temperatureAt the end of this time, the reaction mixture was cooled
  4. stirringthe mixture was shaken
  5. customThe ethyl acetate layer was separated
  6. washwashed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationThe ethyl acetate layer was then concentrated by distillation under reduced pressure
  9. customthe resulting residue was purified by column chromatography through silica gel
  10. additionby volume mixture of methylene chloride and methanol as the eluent

出典と根拠

ORDレコード
ord-45dbebba877446219c3f86b8b1725c1b
出典データセット
uspto-grants-1996_09
特許番号
US05556864

反応ノート

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