Thiazole → HCID 90240746, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence