Ethyl Propionate → 1-(4-Methyl-1,3-thiazol-2-yl)butan-2-one

Temperature

-78 °C

3.00 g (26.5 mmol) of 2,4-dimethylthiazole are dissolved in 30 ml of THF and, at −78° C., 11.6 ml (29.2 mmol) of n-butyllithium (2.5 M solution in hexane) are added dropwise. After stirring at −78° C. for 2 hours, 4.60 g (45.1 mmol) of ethyl propionate are added as solution in 15 ml of abs. THF. The mixture is stirred at −78° C. for 1 h and then warmed to room temperature. It is then hydrolyzed with sodium bicarbonate solution, and the mixture is extracted three times with diethyl ether. The combined organic phases are dried with magnesium sulfate, and the solvent is removed in a rotary evaporator. 3.5 g (39% of theory) of the title compound are obtained in 50% purity (GC-MS) and are employed without further purification.

1. stirringThe mixture is stirred at −78° C. for 1 h
2. temperaturewarmed to room temperature
3. extractionhydrolyzed with sodium bicarbonate solution, and the mixture is extracted three times with diethyl ether
4. dry with materialThe combined organic phases are dried with magnesium sulfate
5. customthe solvent is removed in a rotary evaporator

ORD record

ord-05a91356a4e74a4eab01e9412d141919

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08404723B2