Реакция #160411

Уравнение реакции

ethyl α-bromoisobutyrate

cyclohexyl thiol

KOH

→

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

Выход 83.8%

Растворители

ethanol

Условия реакции

Обработка

1. 1
   ТемператураThe reaction was heated
2. 2
   Температураto reflux for 18 h
3. 3
   ДругоеThe solid (KBr) was separated by filtration
4. 4
   Промывкаrinsed with ethanol (20 mL)
5. 5
   КонцентрированиеThe filtrate was concentrated under reduced pressure
6. 6
   workup.DISSOLUTIONthe residue dissolved in DCM (50 mL)
7. 7
   ПромывкаThe organic layer was washed with water (2×20 mL)
8. 8
   ЭкстракцияThe aqueous washes were back-extracted with DCM (10 mL)
9. 9
   ПромывкаThe combined organics were washed with brine
10. 10
    Сушкаdried over Na2SO4
11. 11
    ФильтрацияFiltration and concentration under reduced pressure

Методика

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.

Источник