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

HRID 244440Notes

Reaction equation

HRID 244440 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-679443ac1cdd4d868822d6830cb934e7
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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