Sodium Chloride → methyl 6-chloro-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate

HRID 67115ノート

反応式

HRID 67115 の反応式
I[CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([Cl:9])[CH:6]=[C:5]1[CH2:10][C:11]([O:13][CH3:14])=[O:12].[Cl-].[Na+]>CN(C)C=O>[Cl:9][C:7]1[CH:6]=[C:5]2[CH:10]([C:11]([O:13][CH3:14])=[O:12])[CH2:2][CH2:3][N:4]2[CH:8]=1

参加物

4

反応物 2

HCID 5234Sodium ChlorideHCID 12795049Methyl 1-(2-iodoethyl)-4-chloropyrrol-2-acetate

生成物 1

HCID 12795078methyl 6-chloro-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

In an atmosphere of argon, 2.52 g. of 50% sodium hydride in mineral oil (0.053 mol.) is washed free of the carrier with dry hexane (2×20 ml.). Thereafter 150 ml. of anhydrous dimethylformamide is added and the mixture is cooled to 0°. To this mixture is added, with stirring, 16.4 g. of methyl 1-(2-iodoethyl)-4-chloropyrrol-2-acetate (0.05 mol.) dissolved in 50 ml. dimethylformamide. The reaction mixture is left at room temperature for 2 hours, when saturated aqueous sodium chloride solution is added and the product extracted into benzene (3×200 ml.). The organic extract is washed with water (2×100 ml.), dried over sodium sulphate and evaporated in vacuo. The crude product (8.52 g.) is purified by column chromatography on silica gel (245 g.) using hexane-ethyl acetate (90:10) as the eluting solvent, to yield methyl 6-chloro-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate, an oil having the following physical constants:

後処理

  1. washof 50% sodium hydride in mineral oil (0.053 mol.) is washed free of the carrier with dry hexane (2×20 ml.)
  2. additionof anhydrous dimethylformamide is added
  3. temperaturethe mixture is cooled to 0°
  4. additionTo this mixture is added
  5. extractionthe product extracted into benzene (3×200 ml.)
  6. extractionThe organic extract
  7. washis washed with water (2×100 ml.)
  8. dry with materialdried over sodium sulphate
  9. customevaporated in vacuo
  10. customThe crude product (8.52 g.) is purified by column chromatography on silica gel (245 g.)

出典と根拠

ORDレコード
ord-3f8c0a8e973042a6bf0bc388e2922452
出典データセット
uspto-grants-1982_08
特許番号
US04344943

反応ノート

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