Acetaldehyde → 1-[3-(Benzyloxy)-6-chloropyridin-2-yl]ethanol

To a solution (100 mL) of 3-(benzyloxy)-6-chloro-2-iodopyridine (17.4 g) synthesized above in tetrahydrofuran was added a 1.0 M solution (60.2 mL) of isopropylmagnesium bromide in tetrahydrofuran at −45° C., and the mixture was stirred at the same temperature for 1 hr. Acetaldehyde (10.2 mL) was added to the reaction mixture, and the mixture was stirred at −45° C. for 30 min then at room temperature for 2 hr. Saturated aqueous ammonium chloride solution was added to quench the reaction, tetrahydrofuran was evaporated in an evaporator, and the residue was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0-30% ethyl acetate/hexane) to give the title object compound (6.82 g, 52%) as a pale-yellow oil.

1. stirringthe mixture was stirred at −45° C. for 30 min
2. waitat room temperature for 2 hr
3. customto quench
4. customthe reaction, tetrahydrofuran
5. customwas evaporated in an evaporator
6. extractionthe residue was extracted with ethyl acetate
7. washThe extract was washed with saturated brine
8. dry with materialdried over magnesium sulfate
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by silica gel column chromatography (0-30% ethyl acetate/hexane)

ORD record

ord-e7af0c71632041d28b15578ba25c0c23

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436043B2