Triacetoxyperiodinane → 1-allyl-4-(2,2,2-trifluoro-acetyl)-1H-pyrrole-2-carbonitrile

HRID 244441Notes

Reaction equation

HRID 244441 reaction equation
[CH2:1]([N:4]1[CH:8]=[C:7]([CH:9]([OH:14])[C:10]([F:13])([F:12])[F:11])[CH:6]=[C:5]1[C:15]#[N:16])[CH:2]=[CH2:3].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([N:4]1[CH:8]=[C:7]([C:9](=[O:14])[C:10]([F:13])([F:11])[F:12])[CH:6]=[C:5]1[C:15]#[N:16])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 594372371-allyl-4-(2,2,2-trifluoro-1-hydroxyethyl)-1H-pyrrole-2-carbonitrile

Product 1

HCID 594372991-allyl-4-(2,2,2-trifluoro-acetyl)-1H-pyrrole-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a room temperature solution of 1-allyl-4-(2,2,2-trifluoro-1-hydroxyethyl)-1H-pyrrole-2-carbonitrile (1.6 g, 7 mmol, 1 equiv.) in 50 mL of CH2Cl2 was added Dess-Martin periodinane (3.6 g, 8.3 mmol, 1.2 equiv). After 3 hours, the reaction was diluted with CH2Cl2 and made basic with saturated NaHCO3. The organic layer was separated and the aqueous extracted with CH2Cl2. The combined organic layers were dried, filtered, and concentrated in vacuo. The residue was purified by flash chromatography using EtOAc-hexanes (0-15% gradient) to provide 1-allyl-4-(2,2,2-trifluoro-acetyl)-1H-pyrrole-2-carbonitrile which was used without further purification.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous extracted with CH2Cl2
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-d4b6632dc2bf46299091ac700277130b
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

Loading…