Phosphate → HCID 14999091, compound

Temperature

0 °C

Dry diisopropylamine (0.95 ml, 5.3 mmol) was added to dry tetrahydrofuran (3 ml). Further a butyllithium solution (3.6 ml, 5.8 mmol) in hexane was added dropwise at -40° C. The mixture was kept at -10° C. for 1 hour. Then a solution of 3,5-dimethyl-2-(3-pyridyl)thiazolidin-4-one (1 g, 4.8 mmol) in dry tetrahydrofuran (7 ml) was added dropwise at -20° to -10° C. After this reaction mixture had been kept between those temperatures for 1 hour, methyl iodide (0.75 g, 5.3 mmol) in dry tetrahydrofuran (2 ml) was added at -20° to -10° C. This reaction mixture was warmed up to 0° C. during 2 hours and then kept at the same temperature for 2 hours. The resulting mixture, after addition of a phosphate buffer (pH 7.0), was extracted with ethyl acetate. The extract was dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated under reduced pressure, and subjected to medium-pressure liquid chromatography (hexane-acetone) and then to recrystallization from a 1 : 1 ether-hexane mixture, giving 5,5,3-trimethyl-2-(3-pyridyl)thiazolidin-4-one (0.42 g, 39% yield).

1. waitAfter this reaction mixture had been kept between those temperatures for 1 hour
2. waitkept at the same temperature for 2 hours
3. extractionwas extracted with ethyl acetate
4. dry with materialThe extract was dried over anhydrous Na2SO4
5. filtrationfiltered
6. concentrationThe filtrate was concentrated under reduced pressure
7. customto recrystallization from a 1 : 1 ether-hexane mixture

ORD record

ord-bb871f7edcd04b619eadf49c3410e1b2

Source dataset

uspto-grants-1991_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05021435