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Diketene → diethyl N-(2,4-dimethoxybenzyl)-3-hydroxy-3-methyl-5-oxo-2,2-pyrrolidine-dicarboxylate

HRID 1719665
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HRID 1719665 반응식
[CH3:1][O:2][C:3]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:4]=1[CH2:5][NH:6][CH:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH2:24]=[C:25]1[O:29][C:27](=[O:28])[CH2:26]1>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:4]=1[CH2:5][N:6]1[C:27](=[O:28])[CH2:26][C:25]([OH:29])([CH3:24])[C:7]1([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:13]([O:15][CH2:16][CH3:17])=[O:14]
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참가 물질

4

반응물 2

HCID 12661DiketeneHCID 13422978Diethyl {[(2,4-dimethoxyphenyl)methyl]amino}propanedioate

생성물 1

HCID 13422981diethyl N-(2,4-dimethoxybenzyl)-3-hydroxy-3-methyl-5-oxo-2,2-pyrrolidine-dicarboxylate수율 60%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

39.6 g (0.122 moles) of diethyl (2,4-dimethoxybenzyl-amino)-malonate prepared according to Example (1c) are boiled with 12.3 g (11.2 ml, 0.146 moles) of diketene in 80 ml of glacial acetic acid for half an hour. The glacial acetic acid is distilled off on a water bath, in vacuo; the residual oil is crystallized by trituration with 150 ml of water, whereupon the substance is dissolved in 60 ml of ethyl acetate and recrystallized by addition of petroleum ether. 29.6 g (60%) of diethyl N-(2,4-dimethoxybenzyl)-3-hydroxy-3-methyl-5-oxo-2,2-pyrrolidine-dicarboxylate and/or the tautomer thereof are obtained.

후처리

  1. distillationThe glacial acetic acid is distilled off on a water bath, in vacuo
  2. customthe residual oil is crystallized by trituration with 150 ml of water, whereupon the substance
  3. dissolutionis dissolved in 60 ml of ethyl acetate
  4. customrecrystallized by addition of petroleum ether

출처 및 근거

ORD 기록
ord-8def80484fb14562b04719554df516c4
출처 데이터셋
uspto-grants-1985_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04541955

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