Water → HCID 21276494, Verbindung

HRID 1381686Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1381686
[C:1]([CH:5]1[C:10](=[O:11])[CH2:9][CH2:8][S:7][CH2:6]1)([O:3][CH3:4])=[O:2].[CH3:12][O:13][CH2:14][CH2:15]Br.O>CS(C)=O>[C:1]([C:5]1([CH2:15][CH2:14][O:13][CH3:12])[C:10](=[O:11])[CH2:9][CH2:8][S:7][CH2:6]1)([O:3][CH3:4])=[O:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 809722-Bromoethyl methyl etherHCID 10374916Methyl 4-oxothiane-3-carboxylate

Produkt 1

HCID 21276494HCID 21276494, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of 5.3 g (25 mmol) of potassium enolate of 4H-2,3,5,6-tetrahydro-3-carbomethoxythiopyran-4-one in 50 ml DMSO, was added 3.47 g (25 mmol) of 2-bromoethyl methyl ether. The solution was stirred under N2 at room temperature for 4 days. The reaction mixture was poured into 500 ml H2O and extracted three times with ethyl acetate. The combined ethyl acetate solution was washed with water; 5% NaOH; H2O and brine; dried over magnesium sulfate, filtered and concentrated in vacuo to give about 5 g crude product. Chromatographed through a pressure column eluting with 10% ethyl acetate-n-hexane to give 2.49 g of the title compound.

Aufarbeitung

  1. extractionextracted three times with ethyl acetate
  2. washThe combined ethyl acetate solution was washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give about 5 g crude product
  7. customChromatographed through a pressure column
  8. washeluting with 10% ethyl acetate-n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-97c781a689a743eea027e1402c36d744
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04803286

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