Reaktion #160411

Reaktionsgleichung

ethyl α-bromoisobutyrate

cyclohexyl thiol

KOH

→

2-cyclohexylsulfanyl-2-methyl-propionic acid ethyl ester

Ausbeute 83.8%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was heated
2. 2
   Temperaturto reflux for 18 h
3. 3
   SonstigeThe solid (KBr) was separated by filtration
4. 4
   Waschenrinsed with ethanol (20 mL)
5. 5
   EinengenThe filtrate was concentrated under reduced pressure
6. 6
   workup.DISSOLUTIONthe residue dissolved in DCM (50 mL)
7. 7
   WaschenThe organic layer was washed with water (2×20 mL)
8. 8
   ExtraktionThe aqueous washes were back-extracted with DCM (10 mL)
9. 9
   WaschenThe combined organics were washed with brine
10. 10
    Trocknendried over Na2SO4
11. 11
    FiltrationFiltration and concentration under reduced pressure

Vorschrift

To a solution of 2.5 g (21.5 mmol) of cyclohexyl thiol in ethanol (75 mL) were added 1.2 g (21.5 mmol) of KOH pellets, followed by 4.2 g (21.5 mmol) of ethyl α-bromoisobutyrate. The reaction was heated to reflux for 18 h and then cooled to room temperature. The solid (KBr) was separated by filtration and rinsed with ethanol (20 mL). The filtrate was concentrated under reduced pressure and the residue dissolved in DCM (50 mL). The organic layer was washed with water (2×20 mL). The aqueous washes were back-extracted with DCM (10 mL). The combined organics were washed with brine, dried over Na2SO4. Filtration and concentration under reduced pressure afforded 4.15 g of 2-cyclohexylsulfanyl-2-methyl-propionic acid ethyl ester.

Quelle