Ethyl formate → HCID 178517725, compound

To δ-valerolactone (2.0 g; 20 mmol) in anhydrous diethyl ether (20 ml) was added ethyl formate (1.6 mL; 21 mmol) and sodium hydride (1.0 g of a 60% w:w dispersion in oil, 25 mmol). The reaction was allowed to stir at room temperature under nitrogen for 45 min. A solution of (2E)-3-phenyl-2-propenimidamide (2.92 g; 20 mmol) in EtOH (25 ml) was added, the mixture was then heated to 80° C. and stirred at this temperature for 4 hours. The reaction was cooled to room temperature, water was added (50 mL) and the mixture was extracted with EtOAc (2×200 mL). The combined organic extracts were dried with Na2SO4, the solvents were removed and the crude residues were purified by column chromatography on silica gel using a 0-10% MeOH/DCM gradient. Fractions containing product were concentrated to afford the desired compound (2.3 g, 45%).

1. temperaturethe mixture was then heated to 80° C.
2. stirringstirred at this temperature for 4 hours
3. temperatureThe reaction was cooled to room temperature
4. extractionthe mixture was extracted with EtOAc (2×200 mL)
5. dry with materialThe combined organic extracts were dried with Na2SO4
6. customthe solvents were removed
7. customthe crude residues were purified by column chromatography on silica gel using a 0-10% MeOH/DCM gradient
8. additionFractions containing product
9. concentrationwere concentrated

ORD record

ord-fe7b2c52cb0c476a9bfc44e2e479c9d4

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07709483B2