Benzaldehyde → HCID 59205196, compound

Temperature

-78 °C

N,N,N′-trimethylethane (1.55 ml, 12 mmol) was dissolved in THF (30 mL) and cooled to −78° C. 2.5 M n-butyllithium (4.4 mL) was then added to the reaction mixture, which was then stirred for 15 min, before addition of pyridine-3-carbaldehyde (0.94 mL, 10 mmol). The reaction mixture was maintained at −78° C. for 15 min, then n-butyllithium (8 mL) was added slowly so that the temperature was always below −42° C. The reaction mixture was stirred for 1 hour at −42° C., then cooled to −78° C. Benzaldehyde (3 mL) was then added slowly into the reaction mixture, which was then stirred for 15 min. The reaction mixture was quenched with ammonium chloride and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and purified by flash chromatography eluted with 5% methanol in dichloromethane to yield 1-phenyl-1,3-dihydro-furo[3,4-c]pyridin-3-ol as a yellow solid.

1. temperatureThe reaction mixture was maintained at −78° C. for 15 min
2. customwas always below −42° C
3. temperaturecooled to −78° C
4. stirringwas then stirred for 15 min
5. customThe reaction mixture was quenched with ammonium chloride
6. extractionextracted with ethyl acetate
7. dry with materialThe organic layer was dried over sodium sulfate
8. custompurified by flash chromatography
9. washeluted with 5% methanol in dichloromethane

ORD record

ord-44aeb2b3bd9f41f1a13852ca2d232b15

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07671065B2