Propanoic acid, 2-bromo-2-methyl-, ethyl ester → 2-Cyclohexylsulfanyl-2-methyl-propionic acid ethyl ester

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.

1. temperatureThe reaction was heated
2. temperatureto reflux for 18 h
3. customThe solid (KBr) was separated by filtration
4. washrinsed with ethanol (20 mL)
5. concentrationThe filtrate was concentrated under reduced pressure
6. dissolutionthe residue dissolved in DCM (50 mL)
7. washThe organic layer was washed with water (2×20 mL)
8. extractionThe aqueous washes were back-extracted with DCM (10 mL)
9. washThe combined organics were washed with brine
10. dry with materialdried over Na2SO4
11. filtrationFiltration and concentration under reduced pressure

ORD-Eintrag

ord-292c8a712f114a24824ba6932dd5b182

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08829034B2