methyl 1-[(4-chlorophenyl)methyl]-2-oxocyclopentane-1-carboxylate

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

Procedure: Tetrahydrofuran (0.72 ml), a 37% formaldehyde aqueous solution (0.242 ml), and potassium carbonate (0.50 mmol) were added to 1-(4-chlorobenzyl)-2-oxocyclopentanecarboxylic acid methyl ester (Compound VI-1) (1.0 mmol), and the mixture was allowed to react at room temperature for 5 hours. Water was added to the resultant reaction solution, and the resultant reaction solution was extracted with ethyl acetate. The organic layer was washed with saturated brine, and thereafter dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified with the use of a silica gel column. In this way, Compound V-1 was obtained. to react at room temperature for 5 hours reaction solution the resultant reaction solution was extracted with ethyl acetate The organic layer was washed with saturated brine dried over anhydrous sodium sulfate The solvent was distilled off the residue was purified with the use of a silica gel column In this way, Compound V-1 was obtained

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

Procedure: 1-(4-Chlorobenzyl)-2-oxo-cyclopentancarboxylic acid methyl ester (Compound No. (XXV)-1, (Compound (XXV), R2=CH3, Ym=4-Cl, A=N) (266.7 mg, 1.00 mmol) was combined with potassium carbonate (69 mg, 0.50 mmol), 37% aqueous solution of formaldehyde (0.242 ml, 3.00 mmol) and THF (0.72 ml) and vigorous stirring was conducted at room temperature for 5 hours. After completion of the reaction, water was added and extraction with ethyl acetate was conducted. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate and the solvent was distilled away. The residue was subjected to silica gel column chromatography (eluent; ethyl acetate:hexane=2:1) for purification to obtain the desired substance. was added extraction with ethyl acetate The organic layer was washed with saturated brine dried over anhydrous sodium sulfate the solvent was distilled away The residue was subjected to silica gel column chromatography (eluent; ethyl acetate:hexane=2:1) for purification to obtain the desired substance

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

Procedure: 1-(4-Chlorobenzyl)-2-oxo-cyclopentancarboxylic acid methyl ester (Compound No. (XXV)-1, (Compound (XXV), R2═CH3, Ym=4-Cl, A=N) (266.7 mg, 1.00 mmol) was combined with potassium carbonate (69 mg, 0.50 mmol), 37% aqueous solution of formaldehyde (0.242 ml, 3.00 mmol) and THF (0.72 ml) and vigorous stirring was conducted at room temperature for 5 hours. After completion of the reaction, water was added and extraction with ethyl acetate was conducted. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate and the solvent was distilled away. The residue was subjected to silica gel column chromatography (eluent; ethyl acetate:hexane=2:1) for purification to obtain the desired substance. was added extraction with ethyl acetate The organic layer was washed with saturated brine dried over anhydrous sodium sulfate the solvent was distilled away The residue was subjected to silica gel column chromatography (eluent; ethyl acetate:hexane=2:1) for purification to obtain the desired substance

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

Procedure: 1-(4-Chlorobenzyl)-2-oxo-cyclopentancarboxylic acid methyl ester (Compound No. (XXV)-1, (Compound (XXV), R2═CH3, Ym=4-Cl, A=N) (266.7 mg, 1.00 mmol) was combined with potassium carbonate (69 mg, 0.50 mmol), 37% aqueous solution of formaldehyde (0.242 ml, 3.00 mmol) and THF (0.72 ml) and vigorous stirring was conducted at room temperature for 5 hours. After completion of the reaction, water was added and extraction with ethyl acetate was conducted. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate and the solvent was distilled away. The residue was subjected to silica gel column chromatography (eluent; ethyl acetate:hexane=2:1) for purification to obtain the desired substance. was added extraction with ethyl acetate The organic layer was washed with saturated brine dried over anhydrous sodium sulfate the solvent was distilled away The residue was subjected to silica gel column chromatography (eluent; ethyl acetate:hexane=2:1) for purification to obtain the desired substance

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

Procedure: 1-(4-Chlorobenzyl)-2-oxo-cyclopentancarboxylic acid methyl ester (Compound No. (XXV)-1, (Compound (XXV), R2═CH3, Ym=4-Cl, A=N) (266.7 mg, 1.00 mmol) was combined with potassium carbonate (69 mg, 0.50 mmol), 37% aqueous solution of formaldehyde (0.242 ml, 3.00 mmol) and THF (0.72 ml) and vigorous stirring was conducted at room temperature for 5 hours. After completion of the reaction, water was added and extraction with ethyl acetate was conducted. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate and the solvent was distilled away. The residue was subjected to silica gel column chromatography (eluent; ethyl acetate:hexane=2:1) for purification to obtain the desired substance. was added extraction with ethyl acetate The organic layer was washed with saturated brine dried over anhydrous sodium sulfate the solvent was distilled away The residue was subjected to silica gel column chromatography (eluent; ethyl acetate:hexane=2:1) for purification to obtain the desired substance

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

Procedure: Tetrahydrofuran (0.72 ml), a 37% formaldehyde aqueous solution (0.242 ml), and potassium carbonate (0.50 mmol) were added to 1-(4-chlorobenzyl)-2-oxocyclopentanecarboxylic acid methyl ester (Compound VI-1) (1.0 mmol), and the mixture was allowed to react at room temperature for 5 hours. Water was added to the resultant reaction solution, and the resultant reaction solution was extracted with ethyl acetate. The organic layer was washed with saturated brine, and thereafter dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified with the use of a silica gel column. In this way, Compound V-1 was obtained. to react at room temperature for 5 hours reaction solution the resultant reaction solution was extracted with ethyl acetate The organic layer was washed with saturated brine dried over anhydrous sodium sulfate The solvent was distilled off the residue was purified with the use of a silica gel column In this way, Compound V-1 was obtained