反应详情

温度

100 °C

To potassium tert-butylate (5.52 g) in tert-butanol (60 cc) heated to 100° C. is added, in the form of a homogeneous solid, a mixture of 3-[(4,6-diphenyl-2-pyridyl)oxy]-1-propanol (5 g) and potassium 2-bromoacetate (4.35 g). The addition is carried out in 1 hour. The reaction mixture is then heated for 48 hours at 100° C. and then poured in iced water (100 g). The pH of the aqueous phase is brought to 5 by addition of 1N hydrochloric acid. The mixture is then extracted with dichloromethane (3×50 cc) after saturating the aqueous phase with sodium chloride. The combined organic phases are dried over sodium sulphate and concentrated to dryness at 40° C. under reduced pressure. The oily residue obtained is purified by chromatography under pressure on silica gel (30-60 mm; eluent: n-hexane-diethyl ether 65-35 and then 40-60 and then diethyl ether-methanol;9-1). The white solid obtained, taken up in acetone (5 cc), is treated with sodium hydroxide pellets (0.19 g) and distilled water (1.cc). The mixture is stirred for 60 hours at room temperature. The precipitate obtained is filtered, washed with ethyl ether and dried at 40° C. under reduced pressure. (white solid; m.p.=285°-288° C.)

1. additionis added, in the form of a homogeneous solid
2. additionThe addition
3. extractionThe mixture is then extracted with dichloromethane (3×50 cc)
4. concentrationafter saturating the aqueous phase with sodium chloride
5. dry with materialThe combined organic phases are dried over sodium sulphate
6. concentrationconcentrated to dryness at 40° C. under reduced pressure
7. customThe oily residue obtained
8. customis purified by chromatography under pressure on silica gel (30-60 mm
9. customThe white solid obtained
10. distillationdistilled water (1.cc)
11. customThe precipitate obtained
12. filtrationis filtered
13. washwashed with ethyl ether
14. customdried at 40° C. under reduced pressure