Methanesulfonyl chloride → Methyl 4-((methylsulfonyl)oxy)tetrahydro-2H-thiopyran-3-carboxylate

HRID 1053963

Reaktionsgleichung

Reaktionsgleichung von HRID 1053963
[OH:1][CH:2]1[CH2:7][CH2:6][S:5][CH2:4][CH:3]1[C:8]([O:10][CH3:11])=[O:9].CCN(C(C)C)C(C)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl.O>[CH3:21][S:22]([O:1][CH:2]1[CH2:7][CH2:6][S:5][CH2:4][CH:3]1[C:8]([O:10][CH3:11])=[O:9])(=[O:24])=[O:23]

Komponenten

6

Edukt 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 10012449Methyl 4-hydroxytetrahydro-2H-thiopyran-3-carboxylate

Produkt 1

HCID 10377614Methyl 4-((methylsulfonyl)oxy)tetrahydro-2H-thiopyran-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of methyl 4-hydroxytetrahydro-2H-thiopyran-3-carboxylate (3.00 g, 17.0 mmol) in DCM (170 mL) was stirred at 0° C. DIPEA (5.95 mL, 34.0 mmol) was added followed by the dropwise addition of methanesulfonyl chloride (1.95 g, 17.0 mmol). The resulting mixture was stirred at 0° C. for 30 minutes then warmed to ambient temperature and stirred for an additional 30 minutes. The mixture was carefully diluted with water and extracted with DCM (2×). The combined organic extracts were washed with 1N aqueous HCl, brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to afford the title compound. The residue was carried forward without further purification.

Aufarbeitung

  1. temperaturethen warmed to ambient temperature
  2. stirringstirred for an additional 30 minutes
  3. extractionextracted with DCM (2×)
  4. washThe combined organic extracts were washed with 1N aqueous HCl, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1626c36fd0ff46adad9d07f3cd360440
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394282B2

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