4'-Chloropropiophenone → HCID 58392487, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence