Thiazole → HCID 90240746, compound

Temperature

0 °C

Isopropylmagnesium chloride/lithium chloride complex (1.3 M, 119 mL, 154 mmol) was added to a flask and cooled to 0° C. and then diluted with 50 mL THF. Thiazole (13.0 g, 154 mmol) was added over 30 minutes making sure the temperature did not exceed 5° C. The orange slurry was stirred for 45 minutes and then cooled to −20° C. and ethyl 4-oxocyclohexane-carboxylate (25.0 g, 147 mmol) in THF (25 mL) was added and then stirred for 50 minutes. The solution was cooled to 5° C. and then quenched with HCl (2 M, 100 mL) and extracted with EtOAc (250 mL). The organic layer was washed with aqueous saturated NaHCO3 solution (100 mL), brine (100 mL), evaporated and purified by flash chromatography on silica gel to afford ethyl 4-hydroxy-4-(1,3-thiazol-2-yl)cyclohexanecarboylate as an oil (23.6 g, 92 mmol).

1. additionIsopropylmagnesium chloride/lithium chloride complex (1.3 M, 119 mL, 154 mmol) was added to a flask
2. customdid not exceed 5° C
3. temperaturecooled to −20° C.
4. stirringstirred for 50 minutes
5. temperatureThe solution was cooled to 5° C.
6. customquenched with HCl (2 M, 100 mL)
7. extractionextracted with EtOAc (250 mL)
8. washThe organic layer was washed with aqueous saturated NaHCO3 solution (100 mL), brine (100 mL)
9. customevaporated
10. custompurified by flash chromatography on silica gel

ORD record

ord-a9874ecad1094354afba6b7b56e13293

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08759366B2