Hydrochloric Acid → 1-[[4-(2-Hydroxyethyl)phenyl]methyl]cyclohexanecarbonitrile

温度

-40 °C

To a mixture maintained under nitrogen, of 5.6 g (54.9 mmoles) of diisopropylamine and 92 ml of dry tetrahydrofuran, cooled to -40° C., there is added dropwise 34.2 ml (54.7 mmoles) of a 1.6M solution of n-butyllithium in hexane, then 8.2 g of 1,3-dimethylimidazolidin-2-one. The mixture is thereafter cooled to -78° C. and is stirred 1/4 hour before adding 5.45 g (50 mmoles) of commercial cyclohexanecarbonitrile in solution in 82 ml of dry tetrahydrofuran. After having stirred 1 hour, at -78° C., 14.3 g (50 mmoles) of the compound prepared in example 26a is added. The temperature is kept for an additional 3 hours at -78° C., before being allowed to rise and the mixture is stirred 19 hours at room temperature. Waster is then added, the mixture is acidified with HCl and is stirred again for 1 hour, before diluting it with water and extracting the reaction mixture with ether. The organic phase, washed with water, dried over Na2SO4 is concentrated. The liquid obtained is purified by distillation to give 7.5 g (yield= 61.6%) of a yellow liquid. b.p.0.5 =130°-80° C.

1. temperatureThe mixture is thereafter cooled to -78° C.
2. stirringAfter having stirred 1 hour, at -78° C.
3. stirringthe mixture is stirred 19 hours at room temperature
4. additionWaster is then added
5. stirringis stirred again for 1 hour
6. extractionextracting the reaction mixture with ether
7. washThe organic phase, washed with water
8. dry with materialdried over Na2SO4
9. concentrationis concentrated
10. customThe liquid obtained
11. distillationis purified by distillation

ORDレコード

ord-e79af58b3a7a4b2a9d3bbdca7fcce1a1

出典データセット

uspto-grants-1995_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05387709