1,8-Diazabicyclo(5.4.0)undec-7-ene → Methyl 5,6-dihydro-2H-thiopyran-3-carboxylate

HRID 1053964Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1053964
CS(O[CH:6]1[CH2:11][CH2:10][S:9][CH2:8][CH:7]1[C:12]([O:14][CH3:15])=[O:13])(=O)=O.C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[S:9]1[CH2:10][CH2:11][CH:6]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH2:8]1

Komponenten

4

Edukt 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10377614Methyl 4-((methylsulfonyl)oxy)tetrahydro-2H-thiopyran-3-carboxylate

Produkt 1

HCID 10351950Methyl 5,6-dihydro-2H-thiopyran-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of methyl 4-((methylsulfonyl)oxy)tetrahydro-2H-thiopyran-3-carboxylate (4.33 g, 17.0 mmol) in DCM (170 mL) was added DBU (3.89 g, 25.5 mmol). The resulting mixture was refluxed at 50° C. for 30 minutes. The mixture was cooled to ambient temperature and washed with 1N aqueous HCl. The organic extract was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by MPLC on silica gel (using a gradient elution of 0-45% EtOAc/hexanes) to afford the title compound. 1H NMR (500 MHz, CDCl3): δ 7.12-7.13 (m, 1H); 3.75 (s, 3H); 3.36 (q, J=2.2 Hz, 2H); 2.68 (t, J=5.8 Hz, 2H); 2.51-2.52 (m, 2H).

Aufarbeitung

  1. temperatureThe mixture was cooled to ambient temperature
  2. washwashed with 1N aqueous HCl
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by MPLC on silica gel (
  9. washa gradient elution of 0-45% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-e2b1eface1b9446091ccf96f4ec4bf9d
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394282B2

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