Water → tert-Butyl 3-bromo-1H-pyrrole-1-carboxylate

HRID 503916

반응식

HRID 503916 반응식
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Br:19][C:20]1[CH:24]=[CH:23][N:22]([Si](C(C)C)(C(C)C)C(C)C)[CH:21]=1.[O:35](C(OC(C)(C)C)=O)[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=O.O>C1COCC1.CN(C1C=CN=CC=1)C>[C:39]([O:38][C:36]([N:22]1[CH:23]=[CH:24][C:20]([Br:19])=[CH:21]1)=[O:35])([CH3:42])([CH3:41])[CH3:40]

참가 물질

7

반응물 4

HCID 962WaterHCID 90495Di-tert-butyl dicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 27633023-Bromo-1-(triisopropylsilyl)pyrrole

생성물 1

HCID 66878053tert-Butyl 3-bromo-1H-pyrrole-1-carboxylate수율 24.2%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of TBAF (1.0 M in THF, 3.6 mL) was added to a solution of 3-bromo-1-triisopropylsilanyl-1H-pyrrole (1.0 g, 3.308 mmol) in THF (10 mL) and the mixture was stirred at room temperature for 30 minutes. (BOC)2O (0.866 g, 3.965 mmol) and DMAP (40 mg, 0.3308 mmol) were added to the reaction and the resulting mixture was stirred for 2 additional hours. Water was added, and the mixture was extracted with EtOAc. The combined organic extracts were washed with water and with brine; dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified via flash chromatography (hexane/EtOAc) to give 0.197 g (24% yield) of 3-bromo-pyrrole-1-carboxylic acid tert-butyl ester as a clear oil.

후처리

  1. stirringthe resulting mixture was stirred for 2 additional hours
  2. extractionthe mixture was extracted with EtOAc
  3. washThe combined organic extracts were washed with water and with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified via flash chromatography (hexane/EtOAc)

출처 및 근거

ORD 기록
ord-b7adad826d1346d2a0b9a67aa0043b68
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776910B2

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