3-(4-methoxyphenyl)propan-1-ol

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:80.01; pressure:0.00; stir:

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

実験手順: To a solution of 3-(p-methoxyphenyl)-1-propanol (16.6 g; 0.1 mol) in 250 mL of tolune, cooled to 0° C., was added dropwise 26 mL of phosphorus tribromide (0.27 mol). Following completion of the addition the reaction was stirred at room temperature for 1 hour, then refluxed for an additional hour. The reaction was cooled and poured onto ice, the layers were separated, and the organic phase washed with saturated sodium bicarbonate (3×) and brine (3×). The crude material obtained upon drying and evaporation of the solvent was chromatographed, eluting with 10%, EtOAc/hexane, to obtain 14 g (61%) of 3-(p-methoxyphenyl)-1-propylbromide. completion of the addition the reaction refluxed for an additional hour The reaction was cooled poured onto ice the layers were separated the organic phase washed with saturated sodium bicarbonate (3×) and brine (3×) The crude material obtained upon drying evaporation of the solvent was chromatographed eluting with 10%, EtOAc/hexane

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

実験手順: 3-(4-Methoxyphenyl)-1-propanol (5.00 g) was dissolved in methylene chloride (50 ml), triphenylphosphine (8.86 g) and N-bromosuccinimide (5.94 g) were added under ice-cooling, and the mixture was stirred under ice-cooling for 1 hr, and further at room temperature for 5 hr. The reaction mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. Diethyl ether (100 ml) was added, and the precipitated triphenylphosphine oxide was filtered off. The concentrate of the filtrate was purified by silica gel column chromatography (hexane:ethyl acetate=100:1-3:1) to give the object product (990 mg) as a colorless oil. cooling cooling for 1 hr The reaction mixture was washed with water and saturated brine dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure Diethyl ether (100 ml) was added the precipitated triphenylphosphine oxide was filtered off The concentrate of the filtrate was purified by silica gel column chromatography (hexane:ethyl acetate=100:1-3:1)

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

実験手順: Under a nitrogen atmosphere, a solution of 8.0 grams (0.048 mole) of 3-(4-methoxyphenyl)propanol and 7.9 grams (0.053 mole) of sodium iodide in 50 mL of acetone was stirred, and 5.7 mL (0.053 mole) of 1-chloroethyl chloroformate was slowly added. Upon completion of addition, the reaction mixture was heated to reflux where it was stirred for four hours. After this time the reaction mixture was cooled, and 50 mL of toluene was added. The acetone was removed by distillation after which the reaction mixture was heated for one hour at reflux in the toluene. The reaction mixture was then cooled and poured into 300 mL of water. The mixture was extracted with 200 mL of diethyl ether. The ether extract was washed with 100 mL of an aqueous 5% sodium thiosulfate solution and then with water. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil, and the oil was dissolved in methylene chloride and filtered through a pad of silica gel. The filtrate was concentrated under reduced pressure to a residual oil. The oil was subjected to column chromatography on silica gel. Elution was accomplished with 40:1 petroleum ether and diethyl ether. The appropriate fractions were combined and concentrated under reduced pressure, yielding 4.3 grams of 3-(4-methoxyphenyl)propyl iodide. The NMR spectrum was consistent with the proposed structure. Upon completion of addition the reaction mixture was heated to reflux where it After this time the reaction mixture was cooled The acetone was removed by distillation after which the reaction mixture was heated for one hour at reflux in the toluene The reaction mixture was then cooled poured into 300 mL of water The mixture was extracted with 200 mL of diethyl ether The ether extract was washed with 100 mL of an aqueous 5% sodium thiosulfate solution The organic layer was dried with magnesium sulfate filtered The filtrate was concentrated under reduced pressure to a residual oil the oil was dissolved in methylene chloride filtered through a pad of silica gel The filtrate was concentrated under reduced pressure to a residual oil Elution concentrated under reduced pressure

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

実験手順: Methanesulfonyl chloride (31 mL) was added dropwise to a solution of 3-(4-methoxyphenyl)-1-propanol (50 g) and triethylamine (56 mL) in dichloromethane (800 mL) at 0° C. The resulting mixture was stirred overnight at room temperature. After washing with water, 2% hydrochloric acid and 4% aqueous sodium bicarbonate, the organic solution was dried over sodium sulfate and rotoevaporated to yield crude 3-(4-methoxyphenyl)-1-propyl methanesulfonate as a colourless solid (ca. 83 g). This product and sodium iodide (75 g) in acetone (800 mL) were heated at reflux in the dark for 20 hours. After cooling to room temperature, the reaction mixture was poured into n-hexane/EtOAc/water 1:1:1 (1.5 L) under stirring. The organic layer was washed with water, diluted aqueous sodium metabisulfite and 4% aqueous sodium bicarbonate, then dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by passing it through a short pad of silica gel (eluting with n-hexane/EtOAc 95:5). The title compound was obtained as a pale yellow solid (75 g). After washing with water, 2% hydrochloric acid and 4% aqueous sodium bicarbonate the organic solution was dried over sodium sulfate

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

実験手順: 4-Methoxybenzenepropanol (7.5 g) and 1,5-dibromopentane (30.5 g) were stirred rapidly at RT with tetra-n-butylammonium bisulphate (1.02 g) and 12.5M aqueous NaOH (36 ml) for 16 h. The mixture was diluted with H2O (170 ml), extracted with ER (3×200 ml) and the combined organic extracts were washed consecutively with H2O (170 ml) and BR (170 ml), dried and evaporated to give an oil (34.8 g). The oil was purified by [FCS] eluting with ER - CX (0:100→4:96) to give the title compound as a colourless oil (8.83 g). T.l.c. (CX-ER 79:1) Rf 0.1. extracted with ER (3×200 ml) the combined organic extracts were washed consecutively with H2O (170 ml) and BR (170 ml) dried evaporated

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

実験手順: 4-Methoxybenzenepropanol (7.5 g) and 1,5-dibromopentane (30.5 g) were stirred rapidly at RT with tetra-n-butylammonium bisulphate (1.02 g) and 12.5M aqueous NaOH (36 ml) for 16 h. The mixture was diluted with H2O (170 ml), extracted with ER (3×200 ml) and the combined organic extracts were washed consecutively with H2O (170 ml) and BR (170 ml), dried and evaporated to give an oil (34.8 g). The oil was purified by [FCS] eluting with ER - CX (0:100→4:96) to give the title compound as a colourless oil (8.83 g). T.l.c. (CX-ER 79:1) Rf 0.1. extracted with ER (3×200 ml) the combined organic extracts were washed consecutively with H2O (170 ml) and BR (170 ml) dried evaporated

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Methyl sulphonyl chloride (12.5 g, 0.11M) was added dropwise to a stirred solution of p-methoxyphenylpropanol (16.6 g, 0.10M) in dichloromethane (60 ml)/pyridine (20 ml) at 0° C. The reaction mixture was maintained at 0° C. for 12 hours, then diluted with dichloromethane (250 ml) and washed with hydrochlorid acid (5×50 ml of 5M.1-1). The solution was washed with water, dried (MgS04) and the solvent was evaporated off under reduced pressure to give 3-(4-methoxyphenyl)propan-1-ol, methane sulphonate (20 g), as a colourless crystalline solid, m.p. 41-42° C. (pentane). washed with hydrochlorid acid (5×50 ml of 5M.1-1) The solution was washed with water dried (MgS04) the solvent was evaporated off under reduced pressure

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

実験手順: A methylene chloride solution (300 mL) of 3-(4-methoxyphenyl)-1-propanol (Aldrich, 15.0 g, 0.090 mol) was cooled to 0° C. and stirred. Pyridinium chlorochromate (Aldrich, 23.4 g, 0.108 mol) was slowly added to the solution which was then warmed to room temperature, placed under a drying tube and stirred over a weekend (approx. 72 hrs.). The reaction mixture was filtered through a pad of Florisil (Aldrich) and the filtrate was concentrated to give the crude product as a dark oil. Purification by flash chromatography (6:1 hexanes:ethyl acetate) gave the desired 3-(4-methoxyphenyl)propionaldehyde as a pale yellow oil. placed under a drying tube stirred over a weekend (approx. 72 hrs.) The reaction mixture was filtered through a pad of Florisil (Aldrich) the filtrate was concentrated to give the crude product as a dark oil Purification by flash chromatography (6:1 hexanes:ethyl acetate)