반응 #648790

반응 방정식

3-(4-chlorophenyl)pentane-1,3-diol

compound

7-[(Methylsulfanyl)methyl]-1H-indole

1-(4-chloropenyl)propan-1-one

indium(III) chloride

→

title compound

3-(4-Chlorophenyl)-3-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}pentan-1-ol

용매

toluene

ethyl acetate

water

ethyl acetate

반응 조건

후처리

1. 1
   온도After cooling to RT
2. 2
   여과the solid was filtered off through kieselguhr
3. 3
   기타The phases of the filtrate were separated
4. 4
   추출the aqueous phase was extracted with ethyl acetate
5. 5
   건조The combined organic phases were dried over sodium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타Purification of the crude product by preparative HPLC (mobile phase: acetonitrile/water gradient)

실험 절차

3.04 g (14.10 mmol) of 3-(4-chlorophenyl)pentane-1,3-diol (preparation in analogy to the synthesis of Example 88A and 89A starting from 1-(4-chloropenyl)propan-1-one and ethyl acetate) and 3.12 g (14.10 mmol) of indium(III) chloride were added to 2.50 g (14.10 mmol) of the compound from Example 8A in 60 ml of toluene. The reaction mixture was stirred at 80° C. for 5 h. After cooling to RT, the reaction solution was mixed with water and ethyl acetate, and the solid was filtered off through kieselguhr. The phases of the filtrate were separated, and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated. Purification of the crude product by preparative HPLC (mobile phase: acetonitrile/water gradient) resulted in 2.13 g (40% of theory) of the title compound.

출처