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

温度

-78 °C

In 300 ml of anhydrous tetrahydrofuran was dissolved 33.2 ml of diisopropylamine, and the solution was cooled to -78° C., to which was added dropwise, while stirring, 148 ml of hexane solution of n-butyl lithium (1.6 M). The mixture was stirred for further 10 minutes at the same temperature, followed by dropwise addition of 20 g of β-picoline. The temperature was then raised up to -10°-0° C. and the mixture was stirred for 20 minutes, to which was added dropwise 19.4 g of ethyl p-anisole dissolved in 40 ml of anhydrous tetrahydrofuran. Then, the mixture was stirred for one hour at room temperature, followed by addition of about 100 ml of water. The organic solvent was evaporated off, and the concentrated solution was subjected to extraction with ethyl acetate. The extract solution was washed with water and dried on magnesium sulfate, followed by crystalliation from a mixture of ethyl acetate-isopropylether to give 20.8 g (yield: 85%) of 1-(4-methoxyphenyl)-2-(3-pyridyl)-ethanone, m.p. 71°-72° C.

1. additionwas added dropwise
2. stirringThe mixture was stirred for further 10 minutes at the same temperature
3. temperatureThe temperature was then raised up to -10°-0° C.
4. stirringthe mixture was stirred for 20 minutes, to which
5. stirringThen, the mixture was stirred for one hour at room temperature
6. customThe organic solvent was evaporated off
7. extractionthe concentrated solution was subjected to extraction with ethyl acetate
8. washThe extract solution was washed with water
9. customdried on magnesium sulfate
10. additionfollowed by crystalliation from a mixture of ethyl acetate-isopropylether

ORDレコード

ord-1cd4ccb5bc3a45e2ab408c62b1b1f9ac

出典データセット

uspto-grants-1986_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04612321