Sodium Methoxide → Methyl 3-oxotetrahydrothiopyran-2-carboxylate

Temperature

80 °C

A 250-mL round bottomed flask was charged with methyl 4-(2-methoxy-2-oxo-ethyl)thiobutanoate (26 g, 126 mmol, 1 eq.), sodium methoxide (30 g, 25 w % in methanol, 139 mmol, 1.1 eq.) and toluene (100 ml). The resulting mixture was stirred at 80° C. overnight and then methanol was removed by distillation until the temperature of the reaction mixture rose to 106° C. After cooling to room temperature, the mixture was poured into a mixture of ice (100 g) and 12N HCl (20 mL). The organic layer was separated and the aqueous layer was extracted with dichloromethane (3×20 ml) and the combined organic layers were dried over Na2SO4. Removal of solvent under reduced pressure gave the title compound as an oil (19.3 g, 88% yield). The product thus obtained was forwarded to the next step without any further purification.

1. custommethanol was removed by distillation until the temperature of the reaction mixture
2. customrose to 106° C
3. temperatureAfter cooling to room temperature
4. additionthe mixture was poured into a mixture of ice (100 g) and 12N HCl (20 mL)
5. customThe organic layer was separated
6. extractionthe aqueous layer was extracted with dichloromethane (3×20 ml)
7. dry with materialthe combined organic layers were dried over Na2SO4
8. customRemoval of solvent under reduced pressure

ORD record

ord-959612c006a04ef3b2b61a8f59fe91dd

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09221843B2