ethyl 3-(4-hydroxyphenyl)prop-2-ynoate

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-iodophenol (22.3 g) in dimethylformamide (200 ml) were added 19.5 ml of ethyl propiolate and 14.8 g of copper (I) oxide, and the reaction solution was stirred at 110° C. for 15 hours. The reaction solution was cooled and then filtered through Celite, and the filtrate was vacuum-concentrated. The residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (4:1)), followed by recrystallization of the purified residue with hexane/ethyl acetate to afford the title compound as a white solid. The reaction solution was cooled filtered through Celite the filtrate was vacuum-concentrated The residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (4:1)) followed by recrystallization of the purified residue with hexane/ethyl acetate

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-iodophenol (22.3 g) in dimethylformamide (200 ml) were added 19.5 ml of ethyl propiolate and 14.8 g of copper (I) oxide, and the reaction solution was stirred at 110° C. for 15 hours. The reaction solution was cooled and then filtered through Celite, and the filtrate was vacuum-concentrated. The residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (4:1)), followed by recrystallization of the purified residue with hexane/ethyl acetate to afford the title compound as a white solid. The reaction solution was cooled filtered through Celite the filtrate was vacuum-concentrated The residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (4:1)) followed by recrystallization of the purified residue with hexane/ethyl acetate

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-iodophenol (22.3 g) in dimethylformamide (200 ml) were added 19.5 ml of ethyl propiolate and 14.8 g of copper (I) oxide, and the reaction solution was stirred at 110° C. for 15 hours. The reaction solution was cooled and then filtered through Celite, and the filtrate was vacuum-concentrated. The residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (4:1)), followed by recrystallization of the purified residue with hexane/ethyl acetate to afford the title compound as a white solid. The reaction solution was cooled filtered through Celite the filtrate was vacuum-concentrated The residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (4:1)) followed by recrystallization of the purified residue with hexane/ethyl acetate

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-iodophenol (22.3 g) in dimethylformamide (200 ml) were added 19.5 ml of ethyl propiolate and 14.8 g of copper (I) oxide, and the reaction solution was stirred at 110° C. for 15 hours. The reaction solution was cooled and then filtered through Celite, and the filtrate was vacuum-concentrated. The residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (4:1)), followed by recrystallization of the purified residue with hexane/ethyl acetate to afford the title compound as a white solid. The reaction solution was cooled filtered through Celite the filtrate was vacuum-concentrated The residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (4:1)) followed by recrystallization of the purified residue with hexane/ethyl acetate