2,2-Difluoro-3-Tetrahydropyranyloxypropyl Trifluoromethanesulfonate → HCID 19937334, Verbindung

HRID 1032918Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1032918
FC(F)(F)S(O[CH2:7][C:8]([F:18])([F:17])[CH2:9][O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)(=O)=O.[C:21]1(=[O:31])[NH:25][C:24](=[O:26])[C:23]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]12.[K]>CN(C)C=O>[F:17][C:8]([F:18])([CH2:7][N:25]1[C:24](=[O:26])[C:23]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]2[C:21]1=[O:31])[CH2:9][O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1

Komponenten

4

Edukt 2

HCID 199373062,2-Difluoro-3-Tetrahydropyranyloxypropyl TrifluoromethanesulfonateHCID 24194345Phthalimide potassium salt

Produkt 1

HCID 19937334HCID 19937334, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A mixture of 2,2-difluoro-3-tetrahydropyranyloxypropyl trifluoromethanesulfonate (2.3 g, 7 mmol), potassium phthalimide (1.4 g, 7.7 mmol) and anhydrous dimethylformamide (50 ml) under nitrogen was stirred and heated at 85° C. overnight. After cooling, salts are filtered off, and the solvent was removed in vacuo. The residue was taken up in dichloromethane (100 ml), washed with 0.5M NaOH (30 ml) and brine. The organic phase was separated, dried over magnesium sulfate and concentrated. The desired compound 2,2-difluoro-3-phthalimido-1-tetrahydropyranyloxypropane was purified by flash chromatography on silica gel (ethyl acetate:hexane; 20:80) (2 g, 90%).

Aufarbeitung

  1. temperatureAfter cooling
  2. filtrationsalts are filtered off
  3. customthe solvent was removed in vacuo
  4. washwashed with 0.5M NaOH (30 ml) and brine
  5. customThe organic phase was separated
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe desired compound 2,2-difluoro-3-phthalimido-1-tetrahydropyranyloxypropane was purified by flash chromatography on silica gel (ethyl acetate:hexane; 20:80) (2 g, 90%)

Quellen und Nachweise

ORD-Eintrag
ord-66ac46dd75a04d0c98c2133c2beed5a8
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05308837

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