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Bromine → Ethyl 1-(2-acetoxyethyl)-4-bromopyrrole-2-glyoxalate

HRID 67113
ノート
印刷プレビュー

反応式

HRID 67113 の反応式
[Br:1]Br.[C:3]([O:6][CH2:7][CH2:8][N:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:5])[CH3:4].CCCCCC.C(OCC)(=O)C>ClCCl>[C:3]([O:6][CH2:7][CH2:8][N:9]1[CH:13]=[C:12]([Br:1])[CH:11]=[C:10]1[C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:5])[CH3:4]
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

5

反応物 3

HCID 24408BromineHCID 12795013Ethyl 1-(2-acetoxyethyl)pyrrole-2-glyoxalateHCID 21226206Ethyl acetate hexane

生成物 1

HCID 12795028Ethyl 1-(2-acetoxyethyl)-4-bromopyrrole-2-glyoxalate収率 56.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-75 °C

実験手順

Three ml (58.3 mmole) of bromine is added in a dropwise manner to a stirred solution of 14.77 g (58.3 mmole) of ethyl 1-(2-acetoxyethyl)pyrrole-2-glyoxalate in 200 ml anhydrous dichloromethane, cooled to -75° C. After the addition, the reaction is left at -75° C. for 2.5 hours and then the temperature is allowed to increase to room temperature. The solvent is removed in vacuo, dichloromethane is added to the residue and the solution is washed successively with water, 10% sodium bicarbonate solution and water. The organic phase is dried over sodium sulfate, and the solvent is removed in vacuo. The crude product thus obtained (18.3 g) is subjected to column chromatography on Florisil (1 Kg) using hexane-ethyl acetate (9:1) as the eluting solvent. There is thus obtained upon removal of the solvent, 10.9 g (56%) of ethyl 1-(2-acetoxyethyl)-4-bromopyrrole-2-glyoxalate as an oil having the following physical constants:

後処理

  1. additionAfter the addition
  2. temperatureto increase to room temperature
  3. customThe solvent is removed in vacuo, dichloromethane
  4. additionis added to the residue
  5. washthe solution is washed successively with water, 10% sodium bicarbonate solution and water
  6. dry with materialThe organic phase is dried over sodium sulfate
  7. customthe solvent is removed in vacuo
  8. customThe crude product thus obtained (18.3 g)

出典と根拠

ORDレコード
ord-00fdc22f138741beb6add2da08e5184d
出典データセット
uspto-grants-1982_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04344943

反応ノート

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