Water → diethyl 1-(2-bromoethyl)-1H-pyrrole-2,4-dicarboxylate

HRID 399436ノート

反応式

HRID 399436 の反応式
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[C:2]1[C:11]([O:13][CH2:14][CH3:15])=[O:12].[H-].[Na+].[Br:18][CH2:19][CH2:20]Br.O>O1CCCC1>[Br:18][CH2:19][CH2:20][N:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[C:2]1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

参加物

6

反応物 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 12711558Diethyl 1H-pyrrole-2,4-dicarboxylate

生成物 1

HCID 18967495diethyl 1-(2-bromoethyl)-1H-pyrrole-2,4-dicarboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of diethyl pyrrole-2,4-dicarboxylate (5.50 g, 29.4 mmol) in tetrahydrofuran (200 ml) was cooled in an ice bath and a suspension of NaH (60%) (6.5 g, 68.6 mmol) in tetrahydro-furan (50 ml) was added in a stream. The reaction flask was warmed to room temperature. After stirring 1 h at room temperature 1,2-dibromoethane (25.2 ml, 294 mmol) was added and the mixture was refluxed for 24 h. Water (50 ml) was added to the reaction flask. The mixture was rotary evaporated to remove tetrahydrofuran. Saturated sodium bicarbonate solution (100 ml) was added to the residue and the resulting solution was extracted with methylene chloride (4×50 ml). The combined organic extracts were dried with anhydrous sodium sulfate. The drying agent was removed by filtration, and the filtrate was rotary evaporated to give a yellow solid. This material was recrystalized from hexane ethyl acetate 80:20 to give 8-2 as a yellow solid.

後処理

  1. additionwas added in a stream
  2. additionwas added
  3. temperaturethe mixture was refluxed for 24 h
  4. customThe mixture was rotary evaporated
  5. customto remove tetrahydrofuran
  6. additionSaturated sodium bicarbonate solution (100 ml) was added to the residue
  7. extractionthe resulting solution was extracted with methylene chloride (4×50 ml)
  8. dry with materialThe combined organic extracts were dried with anhydrous sodium sulfate
  9. customThe drying agent was removed by filtration
  10. customthe filtrate was rotary evaporated
  11. customto give a yellow solid
  12. customThis material was recrystalized from hexane ethyl acetate 80:20

出典と根拠

ORDレコード
ord-f72e5c89509c430f99f2218429ec9e2f
出典データセット
uspto-grants-1998_10
特許番号
US05821241

反応ノート

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