反应详情

To an ice-cold stirred solution of 3-(2-tert-butylphenoxy)azetidine (2.00 g, 9.74 mmol) in pyridine (20.0 ml) was added picolinoyl chloride hydrochloride (2.08 g, 11.7 mmol). After stirring for 16 h at room temperature, the reaction mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and 10% aqueous Na2CO3 and separated. The organic layer was washed with saturated sodium chloride, dried (Na2SO4), filtered by a pad of silica gel and concentrated under reduced pressure. The residue was purified with flash column chromatography (silica gel, 90:10 to 50:50 heptane/ethyl acetate) to provide a yellow solid. The solid was recrystallized from heptane/ethyl acetate to provide (3-(2-tert-butylphenoxy)azetidin-1-yl)(pyridin-2-yl)methanone (0.94 g, 31%) as a off-white solid.

1. concentrationthe reaction mixture was concentrated under reduced pressure
2. customThe residue was partitioned between ethyl acetate and 10% aqueous Na2CO3
3. customseparated
4. washThe organic layer was washed with saturated sodium chloride
5. dry with materialdried (Na2SO4)
6. filtrationfiltered by a pad of silica gel
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified with flash column chromatography (silica gel, 90:10 to 50:50 heptane/ethyl acetate)
9. customto provide a yellow solid
10. customThe solid was recrystallized from heptane/ethyl acetate