3-(3-chloro-2-methylphenyl)prop-2-yn-1-ol

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A suspension of Compound 54-1 (2.58 g) and chlorotris(triphenylphosphine)rhodium(I) (1.50 g) in toluene (80 ml) was stirred under a hydrogen atmosphere at 60° C. for 11 hr. The reaction mixture was filtered through celite and concentrated. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=99:1-80:20) to give the object product (2.11 g) as a brown oil. The reaction mixture was filtered through celite concentrated The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=99:1-80:20)

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A suspension of Compound 54-1 (2.58 g) and chlorotris(triphenylphosphine)rhodium(I) (1.50 g) in toluene (80 ml) was stirred under a hydrogen atmosphere at 60° C. for 11 hr. The reaction mixture was filtered through celite and concentrated. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=99:1-80:20) to give the object product (2.11 g) as a brown oil. The reaction mixture was filtered through celite concentrated The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=99:1-80:20)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2-chloro-6-iodotoluene (5.00 g), copper(I) iodide (75.4 mg), triphenylphosphine (260 mg), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (410 mg), propargyl alcohol (1.29 ml), diisopropylethylamine (13.8 ml) and tetrahydrofuran (100 ml) was stirred at room temperature for 25 hr. The reaction mixture was added to brine, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0-80:20) to give the object product (2.58 g) as a brown oil. the mixture was extracted with ethyl acetate washed with saturated brine dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0-80:20)

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A suspension of Compound 54-1 (2.58 g) and chlorotris(triphenylphosphine)rhodium(I) (1.50 g) in toluene (80 ml) was stirred under a hydrogen atmosphere at 60° C. for 11 hr. The reaction mixture was filtered through celite and concentrated. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=99:1-80:20) to give the object product (2.11 g) as a brown oil. The reaction mixture was filtered through celite concentrated The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=99:1-80:20)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2-chloro-6-iodotoluene (5.00 g), copper(I) iodide (75.4 mg), triphenylphosphine (260 mg), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (410 mg), propargyl alcohol (1.29 ml), diisopropylethylamine (13.8 ml) and tetrahydrofuran (100 ml) was stirred at room temperature for 25 hr. The reaction mixture was added to brine, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0-80:20) to give the object product (2.58 g) as a brown oil. the mixture was extracted with ethyl acetate washed with saturated brine dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0-80:20)