tert-Butanol → Tert-butyl 3-chloropivaloate

Temperature

40 °C

The required 3-Chloro-2,2-dimethyl-propionic acid tert-butyl ester was prepared as follows: To a solution of 3-chloro-2,2-dimethylpropionic acid (5.00 g; 36.6 mmol) in DMF (25 mL) was added N,N′-carbonyldiimidazole (5.94 g; 36.6 mmol) and the resulting mixture was stirred for 1 hour at 40° C. Subsequently, tert-butyl alcohol (7.1 mL; 73 mmol) and DBU (5.5 mL; 36.6 mmol) were added and the mixture stirred overnight at 40° C. After cooling to RT, 5% aqueous NaHCO3 solution (50 mL) was added to the mixture and stirred for another 15 minutes. The reaction mixture was extracted with EtOAc. The organic layer was dried (Na2SO4), concentrated in vacuo and purified by column chromatography (SiO2, Et2O:hexanes 1:1) to afford 3-chloro-2,2-dimethyl-propionic acid tert-butyl ester (3.34 g).

1. customThe required 3-Chloro-2,2-dimethyl-propionic acid tert-butyl ester was prepared
2. stirringthe mixture stirred overnight at 40° C
3. temperatureAfter cooling to RT
4. stirringstirred for another 15 minutes
5. extractionThe reaction mixture was extracted with EtOAc
6. dry with materialThe organic layer was dried (Na2SO4)
7. concentrationconcentrated in vacuo
8. custompurified by column chromatography (SiO2, Et2O:hexanes 1:1)

ORD record

ord-94574042c7f24f3ab764c777f31c1610

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09273017B2