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

HRID 638311ノート

反応式

HRID 638311 の反応式
[H-].[Na+].I[CH2:4][CH2:5][N:6]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]1[CH2:12][C:13]([O:15][CH3:16])=[O:14].[Cl-].[Na+]>CCCCCC.CN(C)C=O>[Cl:11][C:9]1[CH:8]=[C:7]2[CH:12]([C:13]([O:15][CH3:16])=[O:14])[CH2:4][CH2:5][N:6]2[CH:10]=1

参加物

6

反応物 3

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 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 2

HCID 6228Dimethylformamide溶媒2 回HCID 8058Hexane溶媒

実験手順

In an atmosphere of argon, 2.52 g of 50% sodium hydride in mineral oil (0.053 moles) 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 moles) 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. temperaturethe mixture is cooled to 0°
  2. additionTo this mixture is added
  3. extractionthe product extracted into benzene (3×200 ml)
  4. extractionThe organic extract
  5. washis washed with water (2×100 ml)
  6. dry with materialdried over sodium sulphate
  7. customevaporated in vacuo
  8. 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-b7dd588eb3e04fe9ad5a2d180d6585b6
出典データセット
uspto-grants-1985_12
特許番号
US04560699

反応ノート

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