Réaction #160411

Équation de réaction

ethyl α-bromoisobutyrate

cyclohexyl thiol

KOH

→

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

Rendement 83.8%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction was heated
2. 2
   Températureto reflux for 18 h
3. 3
   AutreThe solid (KBr) was separated by filtration
4. 4
   Lavagerinsed with ethanol (20 mL)
5. 5
   ConcentrationThe filtrate was concentrated under reduced pressure
6. 6
   workup.DISSOLUTIONthe residue dissolved in DCM (50 mL)
7. 7
   LavageThe organic layer was washed with water (2×20 mL)
8. 8
   ExtractionThe aqueous washes were back-extracted with DCM (10 mL)
9. 9
   LavageThe combined organics were washed with brine
10. 10
    Séchagedried over Na2SO4
11. 11
    FiltrationFiltration and concentration under reduced pressure

Mode opératoire

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.

Source