ethyl 2-(4-hydroxyphenyl)cyclopropane-1-carboxylate

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

Procedure: Compound 46 was synthesized from (1Z)-2-[4-(hydroxymethyl)phenoxy]-1-(4-methoxyphenyl)ethanone O-methyloxime (0.146 g, 0.48 mmol) and ethyl 2-(4-hydroxyphenyl)cyclopropanecarboxylate (0.1 g, 0.4 mmol) by following the procedure described in scheme 18 (0.01 g, yield: 13.26%); Purity: 92.24%.

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

Procedure: Compound 46 was synthesized from (1Z)-2-[4-(hydroxymethyl)phenoxy]-1-(4-methoxyphenyl)ethanone O-methyloxime (0.146 g, 0.48 mmol) and ethyl 2-(4-hydroxyphenyl)cyclopropanecarboxylate (0.1 g, 0.4 mmol) by following the procedure described in scheme 18 (0.01 g, yield: 13.26%); Purity: 92.24%.

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 50 mL RB flask fitted with magnetic stirrer was charged with 20 mL of dichloromethane. To the stirred solvent was added ethyl 2-(4-methoxyphenyl)cyclopropanecarboxylate (0.9 g, 4 mmol). The reaction mixture was cooled to 0° C. and boron tribromide (0.9 mL) was added drop wise, stirred for 30 minutes at the same temperature. The reaction mixture was quenched by the addition of ethanol drop wise at 0° C. The reaction mixture was concentrated to distill off the solvent; water was added to the crude and extracted with ethyl acetate. The organic layer was washed with saturated solution of NaHCO3 (25 mL), followed by brine solution (25 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as pale yellow liquid (0.3 g, yield: 35.6%). 1H NMR (300 MHz, DMSO-d6): δ 9.27 (s, 1H), 6.94-6.97 (d, 2H), 6.64-6.67 (d, 2H), 4.05-4.12 (q, 2H), 2.28-2.36 (m, 1H), 1.75-1.80 (m, 1H), 1.35-1.41 (m, 2H), 1.15-1.28 (t, 3H). To a 50 mL RB flask fitted with magnetic stirrer The reaction mixture was quenched by the addition of ethanol drop wise at 0° C The reaction mixture was concentrated to distill off the solvent water was added to the crude extracted with ethyl acetate The organic layer was washed with saturated solution of NaHCO3 (25 mL) The organic layer was dried over anhydrous Na2SO4 the solvent was removed under reduced pressure

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

Procedure: Compound 45 was prepared from ethyl 2-(4-hydroxyphenyl)cyclopropanecarboxylate (0.1 g, 0.48 mmol), and 4-{(1Z)-2-[4-(bromomethyl) phenoxy]-N-methoxyethanimidoyl}benzonitrile (0.175 g, 0.48 mmol) by following the procedure described in scheme 17.

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

Procedure: Compound 45 was prepared from ethyl 2-(4-hydroxyphenyl)cyclopropanecarboxylate (0.1 g, 0.48 mmol), and 4-{(1Z)-2-[4-(bromomethyl) phenoxy]-N-methoxyethanimidoyl}benzonitrile (0.175 g, 0.48 mmol) by following the procedure described in scheme 17.

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

Procedure: Compound 46 was synthesized from (1Z)-2-[4-(hydroxymethyl)phenoxy]-1-(4-methoxyphenyl)ethanone O-methyloxime (0.146 g, 0.48 mmol) and ethyl 2-(4-hydroxyphenyl)cyclopropanecarboxylate (0.1 g, 0.4 mmol) by following the procedure described in scheme 18 (0.01 g, yield: 13.26%); Purity: 92.24%.

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 50 mL RB flask fitted with magnetic stirrer was charged with 20 mL of dichloromethane. To the stirred solvent was added ethyl 2-(4-methoxyphenyl)cyclopropanecarboxylate (0.9 g, 4 mmol). The reaction mixture was cooled to 0° C. and boron tribromide (0.9 mL) was added drop wise, stirred for 30 minutes at the same temperature. The reaction mixture was quenched by the addition of ethanol drop wise at 0° C. The reaction mixture was concentrated to distill off the solvent; water was added to the crude and extracted with ethyl acetate. The organic layer was washed with saturated solution of NaHCO3 (25 mL), followed by brine solution (25 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as pale yellow liquid (0.3 g, yield: 35.6%). 1H NMR (300 MHz, DMSO-d6): δ 9.27 (s, 1H), 6.94-6.97 (d, 2H), 6.64-6.67 (d, 2H), 4.05-4.12 (q, 2H), 2.28-2.36 (m, 1H), 1.75-1.80 (m, 1H), 1.35-1.41 (m, 2H), 1.15-1.28 (t, 3H). To a 50 mL RB flask fitted with magnetic stirrer The reaction mixture was quenched by the addition of ethanol drop wise at 0° C The reaction mixture was concentrated to distill off the solvent water was added to the crude extracted with ethyl acetate The organic layer was washed with saturated solution of NaHCO3 (25 mL) The organic layer was dried over anhydrous Na2SO4 the solvent was removed under reduced pressure

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

Procedure: Compound 45 was prepared from ethyl 2-(4-hydroxyphenyl)cyclopropanecarboxylate (0.1 g, 0.48 mmol), and 4-{(1Z)-2-[4-(bromomethyl) phenoxy]-N-methoxyethanimidoyl}benzonitrile (0.175 g, 0.48 mmol) by following the procedure described in scheme 17.