Reaction #160411

Reaction equation

ethyl α-bromoisobutyrate

cyclohexyl thiol

KOH

→

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

Yield 83.8%

Solvents

ethanol

Conditions

Workup

1. 1
   TemperatureThe reaction was heated
2. 2
   Temperatureto reflux for 18 h
3. 3
   OtherThe solid (KBr) was separated by filtration
4. 4
   Washrinsed 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
   WashThe organic layer was washed with water (2×20 mL)
8. 8
   ExtractionThe aqueous washes were back-extracted with DCM (10 mL)
9. 9
   WashThe combined organics were washed with brine
10. 10
    Dryingdried over Na2SO4
11. 11
    FiltrationFiltration and concentration under reduced pressure

Procedure

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