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

HRID 399436노트

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HRID 399436 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f72e5c89509c430f99f2218429ec9e2f
출처 데이터셋
uspto-grants-1998_10
특허 번호
US05821241

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