2,4-Dimethylthiazole → 1-Methoxy-3-(4-methyl-1,3-thiazol-2-yl)acetone

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, 5.32 g (45.1 mmol) of ethyl methoxyacetate 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. 4.2 g (68% of theory) of the title compound are obtained in 80% 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-c80b67ca13a3420cbcf95ad90798a582

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08404723B2