Ethyl butyrate → HCID 59492362, compound

Temperature

-78 °C

3.00 g (26.5 mmol) of 2,4-dimethylthiazole are dissolved in 30 ml of abs. THF and, at −78° C., 11.7 ml (29.2 mmol) of n-butyllithium (2.5 M solution in hexane) are added dropwise. After stirring at −78° C. for 2 hours, 5.23 g (45.1 mmol) of ethyl butyrate 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. The crude product is purified by column chromatography (silica gel, mobile phase: cyclohexane/ethyl acetate 5:1). 3.0 g (62% of theory) of the title compound are obtained.

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
6. customThe crude product is purified by column chromatography (silica gel, mobile phase: cyclohexane/ethyl acetate 5:1)

ORD record

ord-8c9b58ff2e01411e8403ad387c6b5970

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08404723B2