Selenium Dioxide → HCID 58478784, compound

Temperature

100 °C

A solution of 2-methyl-7H-furo[3,4-b]pyridin-5-one (1.41 g, 9.46 mmol) in dioxane (50 mL) is treated with selenium dioxide (1.2 g, 10.8 mmol) and the reaction mixture is heated at 100° C. for 3 h. Additional selenium dioxide (1.2 g, 10.8 mmol) is added at 3 and 6 hours and the reaction mixture is heated at 100° C. The reaction is heated at 100° C. for an additional 42 h. The reaction mixture is filtered through celite and washed with dioxane. The filtrate is concentrated under reduced pressure and subject to chromatography (silica gel, EtOAc/hexane). The high Rf product containing fractions are concentrated to give 5-Oxo-5,7-dihydro-furo[3,4-b]pyridine-2-carbaldehyde (1.23 g, 80%). The low Rf containing fractions are concentrated to give 5-Oxo-5,7-dihydro-furo[3,4-b]pyridine-2-carboxylic acid (159 mg, 9%).

1. temperaturethe reaction mixture is heated at 100° C
2. temperatureThe reaction is heated at 100° C. for an additional 42 h
3. filtrationThe reaction mixture is filtered through celite
4. washwashed with dioxane
5. concentrationThe filtrate is concentrated under reduced pressure
6. additionThe high Rf product containing fractions
7. concentrationare concentrated

ORD record

ord-b3240599312a472aad325e45839a5afc

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977351B2