Trifluoromethanesulfonic anhydride → Methyl 3-(((trifluoromethyl)sulfonyl)oxy)quinoline-8-carboxylate

HRID 472790Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 472790
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].O[C:17]1[CH:18]=[N:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][C:21]=2[C:27]([O:29][CH3:30])=[O:28].C([O-])(O)=O.[Na+]>N1C=CC=CC=1.C(Cl)Cl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:17]1[CH:18]=[N:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][C:21]=2[C:27]([O:29][CH3:30])=[O:28])(=[O:5])=[O:4]

Komponenten

6

Edukt 3

HCID 67749Trifluoromethanesulfonic anhydride2×HCID 516892Sodium BicarbonateHCID 57440941Methyl 3-hydroxyquinoline-8-carboxylate

Produkt 1

HCID 58056975Methyl 3-(((trifluoromethyl)sulfonyl)oxy)quinoline-8-carboxylateAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoromethanesulfonic anhydride (0.55 mL, 3.4 mmol) was added to a solution of methyl 3-hydroxyquinoline-8-carboxylate (650 mg, 3.2 mmol) in pyridine (2.3 mL) and CH2Cl2 (13 mL) at 0° C. The reaction mixture was allowed to warm to room temperature. After 3 h, additional trifluoromethanesulfonic anhydride (0.55 mL, 3.4 mmol) was added and the reaction was stirred for an additional 18 h. Saturated aqueous NaHCO3 (20 mL) was added and the layers were separated. The aqueous phase was extracted with CH2Cl2 (3×). The combined organic phase was dried (MgSO4), filtered and concentrated in vacuo. The resulting residue was purified on silica gel eluting with CH2Cl2 to afford 971 mg (91%) of methyl 3-(((trifluoromethyl)sulfonyl)oxy)quinoline-8-carboxylate.

Aufarbeitung

  1. customthe layers were separated
  2. extractionThe aqueous phase was extracted with CH2Cl2 (3×)
  3. dry with materialThe combined organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified on silica gel eluting with CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-4a8e6bba1a38401f95540a4a7f4a9cd5
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633220B2

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