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Potassium Carbonate → HCID 43091431, Verbindung

HRID 1403683
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1403683
Br[CH:2]1[CH2:6][CH2:5][O:4][C:3]1=[O:7].C([O-])([O-])=O.[K+].[K+].C([O:18][C:19](=[O:22])[CH2:20][SH:21])(C)(C)C>CC#N>[O:7]=[C:3]1[CH:2]([S:21][CH2:20][C:19]([OH:22])=[O:18])[CH2:6][CH2:5][O:4]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 954632(3H)-Furanone, 3-bromodihydro-HCID 113555652-Methyl-2-propanyl sulfanylacetate

Produkt 1

HCID 43091431HCID 43091431, VerbindungAusbeute 133,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 3-bromo-dihydro-furan-2-one (16 g, 97.6 mmol) in 300 mL of CH3CN was added K2CO3 (20 g, 146 mmol), followed by mercapto-acetic acid tert-butyl ester (14.5 g, 98 mmol). The reaction mixture was refluxed for 2 hrs and cooled. The mixture was filtered and the filtrate was concentrated. The residue was redissolved in 300 mL of EtOAc and the resulting solution was washed with 1N HCl (100 mL*2). The organic layer was dried over MaSO4, filtered and concentrated to afford the ter-butyl ester title compound (23 g). 16 g of the ester was dissolved in 250 ml of HCl-MeOH (4M) and stirred at 25° C. for 4 hrs. The reaction mixture was concentrated below 45° C. in vacuum. The residue was purified by column chromatography (EtOAc) to afford 7 g of the title compound.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 2 hrs
  2. temperaturecooled
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was redissolved in 300 mL of EtOAc
  6. washthe resulting solution was washed with 1N HCl (100 mL*2)
  7. customThe organic layer was dried over MaSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7a119bb43c9e4ca699480a88fc0a028f
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08912209B2

Notizen zur Reaktion

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