3-Chloro-1-butene → 3-[(But-2-en-1-yl)sulfanyl]-2-methylfuran

HRID 441621

Reaktionsgleichung

Reaktionsgleichung von HRID 441621
C[O-].[Na+].[CH3:4][C:5]1[O:6][CH:7]=[CH:8][C:9]=1[SH:10].Cl[CH2:12][CH:13]=[CH:14][CH3:15].ClC(C)C=C>CO>[CH2:12]([S:10][C:9]1[CH:8]=[CH:7][O:6][C:5]=1[CH3:4])[CH:13]=[CH:14][CH3:15]

Komponenten

6

Edukt 4

HCID 112423-Chloro-1-buteneHCID 11589Crotyl chlorideHCID 342862-Methyl-3-furanthiolHCID 10942334Sodium Methoxide2×

Produkt 1

HCID 681213633-[(But-2-en-1-yl)sulfanyl]-2-methylfuran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel3×

Reaktionsbedingungen

Temperatur
33 °C

Versuchsvorschrift

Into a 50 ml round bottom 1 neck flask equipped with nitrogen inlet tube, "Y" tube, reflux condenser, magnetic stirrer, and cold water bath is placed a solution containing 0.54 g of sodium methylate (0.01 moles) in 6 ml of anhydrous methanol. 1.14 g (0.01 moles) of 2-methyl-3-furan thiol in 6 ml of anhydrous methanol is then added to the sodium methylate solution. The reaction mass is stirred for a period of 10 minutes, with cooling, maintaining the temperature thereof between 24° and 30° C. 0.91 g (0.01 moles) of a mixture of 80% 1-chloro-2-butene and 20% 3-chloro-1-butene dissolved in 2 ml of anhydrous methanol is then added over a 4 minute period warming to 33° C. The reaction mass is allowed to cool to 23° C. and remains at that temperature, with stirring, for a period of 2.5 hours, at which time it is concentrated to 7 ml on a rotary evaporator using water aspirator vacuum. 20 ml water is then added and the reaction mass is neutralized to a pH of 5 - 6 using 4% hydrochloric acid. The reaction mass is extracted with three 10 ml portions of n-hexane. The hexane extracts are combined, washed with 2 ml saturated sodium chloride solution, dried with anhydrous sodium sulfate and concentrated using a rotary evaporator to yield 1.24 g of a yellow oil.

Aufarbeitung

  1. customInto a 50 ml round bottom 1 neck flask equipped with nitrogen inlet tube
  2. temperature"Y" tube, reflux condenser, magnetic stirrer, and cold water bath
  3. temperaturewith cooling
  4. temperaturemaintaining the temperature
  5. custombetween 24° and 30° C
  6. additionis then added over a 4 minute period
  7. temperatureto cool to 23° C.
  8. stirringwith stirring, for a period of 2.5 hours, at which time it
  9. concentrationis concentrated to 7 ml on a rotary evaporator
  10. addition20 ml water is then added
  11. extractionThe reaction mass is extracted with three 10 ml portions of n-hexane
  12. washwashed with 2 ml saturated sodium chloride solution
  13. dry with materialdried with anhydrous sodium sulfate
  14. concentrationconcentrated
  15. customa rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-87da9dabc1e64d7892bbd0eb705010ab
Quelldatensatz
uspto-grants-1977_08
Patentnummer
US04041186

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