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Water → Diethyl 2-acetoxymethyl-1-benzylimidazole-4,5-dicarboxylate

HRID 265199
ノート
印刷プレビュー

反応式

HRID 265199 の反応式
[C:1]([O-:4])(=[O:3])[CH3:2].[Na+].[CH2:6]([N:13]1[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:16]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[NH:15][C:14]1([CH3:29])Br)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(OCC)(=O)C.O>CN(C)C=O>[C:1]([O:4][CH2:29][C:14]1[N:13]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:16]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:15]=1)(=[O:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 517045Sodium AcetateHCID 70219750Diethyl 1-benzyl-2-bromo-methylimidazole-4,5-dicarboxylate

生成物 1

HCID 19036167Diethyl 2-acetoxymethyl-1-benzylimidazole-4,5-dicarboxylate収率 60.4%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
40 °C

実験手順

1.11 g of sodium acetate were added to a solution of 2.67 g of diethyl 1-benzyl-2-bromomethylimidazole-4,5-dicarboxylate [prepared as described in Preparation 42(ii)] in 30 ml of dimethylformamide, and the resulting mixture was heated at 40° C. for 5 hours. At the end of this time, the reaction solution was mixed with ethyl acetate and water, and then the ethyl acetate layer was separated. The resulting ethyl acetate extract was washed with an aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 1.52 g of the title compound as a syrup.

後処理

  1. customthe ethyl acetate layer was separated
  2. extractionThe resulting ethyl acetate extract
  3. washwas washed with an aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was then removed by distillation under reduced pressure
  6. customThe residue was purified by column chromatography through silica gel
  7. additionby volume mixture of hexane and ethyl acetate as the eluent

出典と根拠

ORDレコード
ord-9182ce1639a7418f994ca27831807a13
出典データセット
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05646171

反応ノート

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