二苯基硫代甲烷

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Diphenylmethanethiol (297 mg) was dissolved in DMF (2 ml) and potassium t-butoxide (166 mg) was added to the obtained solution, followed by stirring the resulting solution at room temperature for 5 minutes. To this reaction solution, a solution of 3-(2-bromoethyl)-7-tetrahydropyranyloxybenzofuran (335 mg) in DMF (2.5 ml) was added dropwise for 5 minutes, and the resulting solution was stirred at room temperature for 15 minutes. To this reaction solution, 1N hydrochloric acid (1.5 ml) was added and the solution was stirred at room temperature for 1 hour. The reaction mixture was poured into water layer (50 ml) and the resultant was extracted twice with ethyl acetate (20 ml). The organic layers were combined and washed with saturated brine, followed by drying over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the obtained residue was dissolved in DMF (4 ml). To this solution, potassium carbonate (205 mg) and methyl bromoacetate (0.19 ml) were added and the resulting mixture was stirred at room temperature for 3.5 hours. The reaction solution was poured into water layer (50 ml) and the resultant was extracted twice with ethyl acetate (20 ml). The organic layers were combined and washed with saturated saline, followed by drying over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: hexane/ethyl acetate=3/1) using silica gel to obtain the desired compound (255 mg, yield: 60%). the resulting solution was stirred at room temperature for 15 minutes the solution was stirred at room temperature for 1 hour the resultant was extracted twice with ethyl acetate (20 ml) washed with saturated brine by drying over sodium sulfate After removing the sodium sulfate by filtration the solvent was removed under reduced pressure the obtained residue was dissolved in DMF (4 ml) To this solution, potassium carbonate (205 mg) and methyl bromoacetate (0.19 ml) were added the resulting mixture was stirred at room temperature for 3.5 hours The reaction solution was poured into water layer (50 ml) the resultant was extracted twice with ethyl acetate (20 ml) washed with saturated saline by drying over sodium sulfate After removing the sodium sulfate by filtration the solvent was removed under reduced pressure the residue was purified by column chromatography (solvent: hexane/ethyl acetate=3/1)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Under argon atmosphere, diphenylmethanethiol (121 mg) was dissolved in DMF (2 ml) and the solution was stirred at room temperature. To this solution, potassium t-butoxide (81 mg) and 3-chloromethyl-7-methoxybenzofuran (118 mg) were added and the solution was stirred at room temperature. After confirming vanishment of the materials, the reaction solution was poured into saturated aqueous ammonium chloride solution (5 ml) and the resulting solution was extracted three times with ethyl acetate (10 ml). The organic layers were combined and washed with saturated brine, followed by drying the resultant over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: hexane/ethyl acetate=20/1) using silica gel to obtain the desired compound (183 mg, yield: 85%). the solution was stirred at room temperature the resulting solution was extracted three times with ethyl acetate (10 ml) washed with saturated brine by drying the resultant over sodium sulfate After removing the sodium sulfate by filtration the solvent was removed under reduced pressure the residue was purified by column chromatography (solvent: hexane/ethyl acetate=20/1)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Under argon atmosphere, diphenylmethanethiol (121 mg) was dissolved in DMF (2 ml) and the solution was stirred at room temperature. To this solution, potassium t-butoxide (81 mg) and 3-chloromethyl-7-methoxybenzofuran (118 mg) were added and the solution was stirred at room temperature. After confirming vanishment of the materials, the reaction solution was poured into saturated aqueous ammonium chloride solution (5 ml) and the resulting solution was extracted three times with ethyl acetate (10 ml). The organic layers were combined and washed with saturated brine, followed by drying the resultant over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: hexane/ethyl acetate=20/1) using silica gel to obtain the desired compound (183 mg, yield: 85%). the solution was stirred at room temperature the resulting solution was extracted three times with ethyl acetate (10 ml) washed with saturated brine by drying the resultant over sodium sulfate After removing the sodium sulfate by filtration the solvent was removed under reduced pressure the residue was purified by column chromatography (solvent: hexane/ethyl acetate=20/1)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Diphenylmethanethiol (297 mg) was dissolved in DMF (2 ml) and potassium t-butoxide (166 mg) was added to the obtained solution, followed by stirring the resulting solution at room temperature for 5 minutes. To this reaction solution, a solution of 3-(2-bromoethyl)-7-tetrahydropyranyloxybenzofuran (335 mg) in DMF (2.5 ml) was added dropwise for 5 minutes, and the resulting solution was stirred at room temperature for 15 minutes. To this reaction solution, 1N hydrochloric acid (1.5 ml) was added and the solution was stirred at room temperature for 1 hour. The reaction mixture was poured into water layer (50 ml) and the resultant was extracted twice with ethyl acetate (20 ml). The organic layers were combined and washed with saturated brine, followed by drying over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the obtained residue was dissolved in DMF (4 ml). To this solution, potassium carbonate (205 mg) and methyl bromoacetate (0.19 ml) were added and the resulting mixture was stirred at room temperature for 3.5 hours. The reaction solution was poured into water layer (50 ml) and the resultant was extracted twice with ethyl acetate (20 ml). The organic layers were combined and washed with saturated saline, followed by drying over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: hexane/ethyl acetate=3/1) using silica gel to obtain the desired compound (255 mg, yield: 60%). the resulting solution was stirred at room temperature for 15 minutes the solution was stirred at room temperature for 1 hour the resultant was extracted twice with ethyl acetate (20 ml) washed with saturated brine by drying over sodium sulfate After removing the sodium sulfate by filtration the solvent was removed under reduced pressure the obtained residue was dissolved in DMF (4 ml) To this solution, potassium carbonate (205 mg) and methyl bromoacetate (0.19 ml) were added the resulting mixture was stirred at room temperature for 3.5 hours The reaction solution was poured into water layer (50 ml) the resultant was extracted twice with ethyl acetate (20 ml) washed with saturated saline by drying over sodium sulfate After removing the sodium sulfate by filtration the solvent was removed under reduced pressure the residue was purified by column chromatography (solvent: hexane/ethyl acetate=3/1)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Under argon atmosphere, diphenylmethanethiol (121 mg) was dissolved in DMF (2 ml) and the solution was stirred at room temperature. To this solution, potassium t-butoxide (81 mg) and 3-chloromethyl-7-methoxybenzofuran (118 mg) were added and the solution was stirred at room temperature. After confirming vanishment of the materials, the reaction solution was poured into saturated aqueous ammonium chloride solution (5 ml) and the resulting solution was extracted three times with ethyl acetate (10 ml). The organic layers were combined and washed with saturated brine, followed by drying the resultant over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: hexane/ethyl acetate=20/1) using silica gel to obtain the desired compound (183 mg, yield: 85%). the solution was stirred at room temperature the resulting solution was extracted three times with ethyl acetate (10 ml) washed with saturated brine by drying the resultant over sodium sulfate After removing the sodium sulfate by filtration the solvent was removed under reduced pressure the residue was purified by column chromatography (solvent: hexane/ethyl acetate=20/1)