Ethyl isobutyrate → ethyl 4-chloro-2,2-dimethylbutyrate

Temperature

-78 °C

To a solution of 22.2 ml of diisopropylamine in 150 ml of tetrahydrofuran was added 93.6 ml of 1.6M n-butyllithium-hexane with stirring at -5° to 0° C. and the mixture was stirred for 30 minutes. The reaction mixture was cooled to -78° C. and 19.0 ml of ethyl isobutyrate was added dropwise. The mixture was then further stirred for 45 minutes, after which a solution of 11.9 ml of 1-bromo-2-chloroethane in 10 ml of tetrahydrofuran was added dropwise. The reaction mixture was stirred at -78° C. for 1 hour and, then, at room temperature for 2 hours. After an excess amount of an aqueous solution of ammonium chloride was added, the mixture was extracted with ethyl acetate. The extract was washed with water and dried (MgSO4) and the solvent was distilled off. Finally, the residue was distilled under reduced pressure to provide 24.7 g of the title compound as colorless oil. b.p. 54°-56° C./0.25 mmHg

1. stirringthe mixture was stirred for 30 minutes
2. stirringThe mixture was then further stirred for 45 minutes
3. stirringThe reaction mixture was stirred at -78° C. for 1 hour
4. extractionthe mixture was extracted with ethyl acetate
5. washThe extract was washed with water
6. dry with materialdried (MgSO4)
7. distillationthe solvent was distilled off
8. distillationFinally, the residue was distilled under reduced pressure

ORD record

ord-d14a21dacd524020aba072abd67a3de3

Source dataset

uspto-grants-1995_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05389633