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

HRID 244441노트

반응식

HRID 244441 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d4b6632dc2bf46299091ac700277130b
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658637B2

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