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

HRID 503916

反応式

HRID 503916 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b7adad826d1346d2a0b9a67aa0043b68
出典データセット
uspto-grants-2010_08
特許番号
US07776910B2

関連ノート

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