Diisopropylamine → 1-(4-Methoxyphenyl)-2-(pyridin-3-yl)ethanone

Temperature

-5 °C

A solution of diisopropylamine (33.2 mL) in anhydrous tetrahydrofuran (300 mL) was cooled to −78° C. and a 1.6 M n-butyllithium/hexane solution (148 mL) was added dropwise with stirring. After completion of dropwise addition, the mixture was stirred for 10 min at the same temperature, and then β-picoline (20 g) was added dropwise. The temperature was raised to −10-0° C., and after stirring for 20 min, a solution of ethyl p-anisate (19.4 g) in anhydrous tetrahydrofuran (40 mL) was added dropwise. After completion of dropwise addition, the mixture was stirred at room temperature for 1 h, and water (100 mL) was added. The organic solvent was evaporated under reduced pressure and an oily product was extracted with ethyl acetate. The extract was washed with water, and after drying, the solvent was evaporated. The remaining crude crystals were recrystallized from ethyl acetate-isopropyl ether to give the title compound (20.8 g, yield 85%). melting point: 71-72° C.

1. additionAfter completion of dropwise addition
2. stirringthe mixture was stirred for 10 min at the same temperature
3. stirringafter stirring for 20 min
4. additionAfter completion of dropwise addition
5. stirringthe mixture was stirred at room temperature for 1 h
6. customThe organic solvent was evaporated under reduced pressure
7. extractionan oily product was extracted with ethyl acetate
8. washThe extract was washed with water
9. customafter drying
10. customthe solvent was evaporated
11. customThe remaining crude crystals were recrystallized from ethyl acetate-isopropyl ether

ORD record

ord-af812bb2d506490faa7e2fcae8a1e167

Source dataset

uspto-grants-2005_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06962933B1