Chloroacetamide → Ethyl 2,5-dioxo-3-pyrrolidinecarboxylate

HRID 1675928

反応式

HRID 1675928 の反応式
[O-]CC.[Na+].C(O)C.[C:8]([O:16][CH2:17][CH3:18])(=[O:15])[CH2:9][C:10]([O:12]CC)=O.Cl[CH2:20][C:21]([NH2:23])=[O:22]>C(O)C>[O:12]=[C:10]1[CH:9]([C:8]([O:16][CH2:17][CH3:18])=[O:15])[CH2:20][C:21](=[O:22])[NH:23]1

参加物

5

反応物 3

HCID 6580ChloroacetamideHCID 7761Diethyl MalonateHCID 23706232Ethanol sodium ethoxide

生成物 1

HCID 23635561Ethyl 2,5-dioxo-3-pyrrolidinecarboxylate収率 66%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

To a solution of 20% sodium ethoxide•ethanol solution (34.0 g) diluted with ethanol (40 ml) was added a solution of diethyl malonate (16.0 g) in ethanol (40 ml) dropwise over 30 minutes in ice-cooling. After stirring in ice-cooling for additional 30 minutes, thereto was added 2-chloroacetamide (4.7 g) in one portion and the mixture was stirred in ice-cooling for 30 minutes and then at room temperature for 20 hours. The white solid precipitated was collected by filtering and washed with a small amount of ethanol. This white solid was dissolved in water (300 ml) and this resulting aqueous solution was acidified with conc. hydrochloric acid and extracted with dichloromethane (50 ml) three times. The extract was dried over magnesium sulfate, filtered and concentrated to give a yellow oil. This was purified by a flash column chromatography (n-hexane:ethyl acetate=2:1→1:1) to give ethyl 2,5-dioxopyrrolidine-3-carboxylate (5.63 g, 66%).

後処理

  1. temperaturecooling
  2. temperaturecooling for additional 30 minutes
  3. stirringthe mixture was stirred in ice-
  4. temperaturecooling for 30 minutes
  5. customThe white solid precipitated
  6. customwas collected
  7. filtrationby filtering
  8. washwashed with a small amount of ethanol
  9. dissolutionThis white solid was dissolved in water (300 ml)
  10. extractionextracted with dichloromethane (50 ml) three times
  11. dry with materialThe extract was dried over magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customto give a yellow oil
  15. customThis was purified by a flash column chromatography (n-hexane:ethyl acetate=2:1→1:1)

出典と根拠

ORDレコード
ord-5029ec1424ee4cc980e882fd000a04b8
出典データセット
uspto-grants-2011_08
特許番号
US08003808B2

関連ノート

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