(Trifluoromethyl)trimethylsilane → 1-allyl-4-(2,2,2-trifluoro-1-hydroxyethyl)-1H-pyrrole-2-carbonitrile

HRID 244440ノート

反応式

HRID 244440 の反応式
[CH2:1]([N:4]1[CH:8]=[C:7]([CH:9]=[O:10])[CH:6]=[C:5]1[C:11]#[N:12])[CH:2]=[CH2:3].[C:13]([Si](C)(C)C)([F:16])([F:15])[F:14].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:1]([N:4]1[CH:8]=[C:7]([CH:9]([OH:10])[C:13]([F:16])([F:15])[F:14])[CH:6]=[C:5]1[C:11]#[N:12])[CH:2]=[CH2:3]

参加物

5

反応物 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 212784831-allyl-4-formyl-1H-pyrrole-2-carbonitrile

生成物 1

HCID 594372371-allyl-4-(2,2,2-trifluoro-1-hydroxyethyl)-1H-pyrrole-2-carbonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a chilled (0° C.) solution of 1-allyl-4-formyl-1H-pyrrole-2-carbonitrile (1.25 g, 7.8 mmol, 1 equiv.) in 10 mL of THF was added CF3TMS (1.5 ml, 9.5 mmol, 1.2 equiv.) dropwise followed by TBAF (1M in THF, 9.4 ml, 9.4 mmol, 1.2 equiv.) slowly dropwise. The cold bath was then removed and the mixture was stirred at room temperature. After 2 hours, the reaction was quenched with water and extracted with EtOAc. The organic was dried, filtered, and concentrated in vacuo. The residue was purified by flash chromatography eluting with EtOAc-hexanes (5-40% gradient) to afford 1-allyl-4-(2,2,2-trifluoro-1-hydroxyethyl)-1H-pyrrole-2-carbonitrile which was used without further purification.

後処理

  1. customThe cold bath was then removed
  2. customthe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. customThe organic was dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography
  8. washeluting with EtOAc-hexanes (5-40% gradient)

出典と根拠

ORDレコード
ord-679443ac1cdd4d868822d6830cb934e7
出典データセット
uspto-grants-2014_02
特許番号
US08658637B2

反応ノート

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