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Hydrochloric Acid → HCID 13343383, Verbindung

HRID 278059
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 278059
[CH:1](NC(C)C)(C)C.C([Li])CCC.[CH:13]([S:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])([CH3:15])[CH3:14].CI.Cl>O1CCCC1>[CH:13]([S:16][CH:17]([CH3:1])[C:18]([O:20][CH2:21][CH3:22])=[O:19])([CH3:15])[CH3:14]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 10773300Ethyl (isopropylthio)acetateHCID 178418339Butyllithium

Produkt 1

HCID 13343383HCID 13343383, VerbindungAusbeute 56,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of diisopropylamine (15.4 mL, 0.11 mol) in tetrahydrofuran is cooled to 0° C., treated dropwise with a 2.04 M solution of n-butyllithium in tetrahydro-furan (51.4 mL, 0.105 mol), stirred at 0° C. for 30 minutes, treated dropwise with ethyl (isopropylthio)acetate (16.3 g, 0.1 mol), stirred at 0° C. for 1 hour, treated with methyl iodide (15.6 g, 0.11 mol), stirred at room temperature for 20 hours, and poured into an ice-water mixture (100 g) containing 15 mL of 6 N hydrochloric acid. The resulting aqueous mixture is extracted with ether. The combined organic extracts are washed sequentially with water, saturated sodium thiosulfate solution, water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a brown solution. Vacuum distillation of the brown solution gives the title product as a liquid (10.0 g) which is identified by NMR spectral analysis.

Aufarbeitung

  1. stirringstirred at 0° C. for 1 hour
  2. stirringstirred at room temperature for 20 hours
  3. extractionThe resulting aqueous mixture is extracted with ether
  4. washThe combined organic extracts are washed sequentially with water, saturated sodium thiosulfate solution, water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain a brown solution
  8. distillationVacuum distillation of the brown solution

Quellen und Nachweise

ORD-Eintrag
ord-602d2a9ccfa54643b5b62f3048cb3e1c
Quelldatensatz
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06359009B1

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