Carbon Dioxide → Ethyl 1-(2-acetoxyethyl)-4-chloropyrrole-2-glycolate

HRID 67114ノート

反応式

HRID 67114 の反応式
C(=O)=O.[BH4-].[Na+].[C:6]([O:9][CH2:10][CH2:11][N:12]1[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13]1[C:18](=[O:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[O:8])[CH3:7]>CO.O.C(O)(=O)C.C(Cl)(Cl)(Cl)Cl>[C:6]([O:9][CH2:10][CH2:11][N:12]1[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13]1[CH:18]([OH:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[O:8])[CH3:7]

参加物

8

反応物 3

HCID 280Carbon DioxideHCID 4311764Sodium borohydrideHCID 12795026Ethyl 1-(2-acetoxyethyl)-4-chloropyrrole-2-glyoxalate

生成物 1

HCID 12795036Ethyl 1-(2-acetoxyethyl)-4-chloropyrrole-2-glycolate

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒2 回HCID 962Water溶媒2 回HCID 5943Carbon Tetrachloride溶媒

実験手順

A solution of water (25 ml.) in methanol (300 ml.) is cooled in a dry ice:carbon tetrachloride:acetone bath to -30° and 23.7 g. of sodium borohydride is added thereto. When the violent reaction has subsided, there is added, in a drop wise manner, 40 g. (0.139 mol.) of ethyl 1-(2-acetoxyethyl)-4-chloropyrrole-2-glyoxalate dissolved in methanol (400 ml.) at a rate such that the temperature does not exceed -20°. The reaction is maintained at this temperature for two hours when there is added a solution of 21.5 ml. of acetic acid in 320 ml. water. The solution is stirred for a further 1 hour at -30° during which time a white precipitate forms. This solid is collected by filtration and dissolved in dichloromethane. The organic solution was washed with saturated sodium chloride solution, dried over sodium sulphate and evaporated in vacuo. There is obtained 33.15 g. of a solid product which is homogeneous by thin layer chromatography. Recrystallization from dichloromethane-hexane yields ethyl 1-(2-acetoxyethyl)-4-chloropyrrole-2-glycolate, m.p. 60°-61° C. (Formula VI where Y is Cl).

後処理

  1. customto -30°
  2. customWhen the violent reaction
  3. additionthere is added, in a drop wise manner, 40 g
  4. customdoes not exceed -20°
  5. temperatureThe reaction is maintained at this temperature for two hours when there
  6. additionis added a solution of 21.5 ml
  7. filtrationThis solid is collected by filtration
  8. dissolutiondissolved in dichloromethane
  9. washThe organic solution was washed with saturated sodium chloride solution
  10. dry with materialdried over sodium sulphate
  11. customevaporated in vacuo
  12. customThere is obtained 33.15 g
  13. customRecrystallization from dichloromethane-hexane

出典と根拠

ORDレコード
ord-da7d7909125a46d69abc1bd7fc57c349
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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