ethyl 3-(4-chlorophenyl)-3-hydroxybutanoate

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.42 g (14.10 mmol) of ethyl 3-(4-chlorophenyl)-3-hydroxybutanoate (preparation in analogy to the synthesis of Example 88A starting from 4-chloroacetophenone 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 100 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. 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 flash chromatography on silica gel (mobile phase: dichloromethane/methanol 95/5) and then by preparative HPLC (mobile phase: acetonitrile/water gradient) resulted in 0.98 g (17% of theory) of the title compound. to the synthesis of Example 88A After cooling to RT the solid was filtered off The phases of the filtrate were separated the aqueous phase was extracted with ethyl acetate The combined organic phases were dried over sodium sulfate filtered concentrated Purification of the crude product by flash chromatography on silica gel (mobile phase: dichloromethane/methanol 95/5)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.42 g (14.10 mmol) of ethyl 3-(4-chlorophenyl)-3-hydroxybutanoate (preparation in analogy to the synthesis of Example 88A starting from 4-chloroacetophenone 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 100 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. 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 flash chromatography on silica gel (mobile phase: dichloromethane/methanol 95/5) and then by preparative HPLC (mobile phase: acetonitrile/water gradient) resulted in 0.98 g (17% of theory) of the title compound. to the synthesis of Example 88A After cooling to RT the solid was filtered off The phases of the filtrate were separated the aqueous phase was extracted with ethyl acetate The combined organic phases were dried over sodium sulfate filtered concentrated Purification of the crude product by flash chromatography on silica gel (mobile phase: dichloromethane/methanol 95/5)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.42 g (14.10 mmol) of ethyl 3-(4-chlorophenyl)-3-hydroxybutanoate (preparation in analogy to the synthesis of Example 88A starting from 4-chloroacetophenone 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 100 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. 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 flash chromatography on silica gel (mobile phase: dichloromethane/methanol 95/5) and then by preparative HPLC (mobile phase: acetonitrile/water gradient) resulted in 0.98 g (17% of theory) of the title compound. to the synthesis of Example 88A After cooling to RT the solid was filtered off The phases of the filtrate were separated the aqueous phase was extracted with ethyl acetate The combined organic phases were dried over sodium sulfate filtered concentrated Purification of the crude product by flash chromatography on silica gel (mobile phase: dichloromethane/methanol 95/5)