Ethyl formate → HCID 178517725, Verbindung

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 70° 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 70° 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-Eintrag

ord-423ad709c1ba4a14911e6864038dd065

Quelldatensatz

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08071592B2