反应详情

温度

50 °C

1-(4-Chloro-phenoxy)-propan-2-one (2.66 g) was added to a stirred solution of [4-(methylthio)phenyl]-hydrazine hydrochloride (2.5 g) in MeCN (15 ml)/HCl (0.5M, 15 ml) at RT. The reaction was stirred at 50° C. for 1 h. After cooling to room temperature, the reaction was partitioned between ethylacetate/water, the organics were separated, washed with aq sodium hydroxide (1 M), dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 5-20% ethylacetate/iso-hexane. The resulting hydrazone was dissolved in THF (80 ml). Sodium bicarbionate solid (1.04 g) was added followed by phosphorus trichloride (0.41 ml) dropwise, and the reaction stirred at RT for 2 h. Further phosphorus trichloride (1.20 ml) was added dropwise, and the reaction stirred at RT for 16 h. The reaction was quenched with water. The mixture was extracted with ethylacetate, the organics washed with aq. sodium hydrogencarbonate, brine, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 5-10% ethylacetate/iso-hexane. Yield 0.45 g.

1. temperatureAfter cooling to room temperature
2. customthe reaction was partitioned between ethylacetate/water
3. customthe organics were separated
4. washwashed with aq sodium hydroxide (1 M)
5. customdried
6. customevaporated under reduced pressure
7. customThe residue was purified by chromatography on silica eluting with 5-20% ethylacetate/iso-hexane
8. dissolutionThe resulting hydrazone was dissolved in THF (80 ml)
9. additionSodium bicarbionate solid (1.04 g) was added
10. stirringthe reaction stirred at RT for 2 h
11. additionFurther phosphorus trichloride (1.20 ml) was added dropwise
12. stirringthe reaction stirred at RT for 16 h
13. customThe reaction was quenched with water
14. extractionThe mixture was extracted with ethylacetate
15. washthe organics washed with aq. sodium hydrogencarbonate, brine
16. customdried
17. customevaporated under reduced pressure
18. customThe residue was purified by chromatography on silica eluting with 5-10% ethylacetate/iso-hexane