5-phenylpentan-1-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Phosphorus tribromide (4.7 ml, 49.8 mmol) was added dropwise to a solution of 5-phenylpentan-1-ol (3 ml, 17.8 mmol) in dioxane (70 ml). The reaction mixture was stirred for 2 hours at room temperature. Another portion of phosphorus tribromide (4.7 m. 49.8 mmol) was added. The reaction mixture was stirred for 16 h at room temprature. It was cooled to 0° C. Water (60 ml) was added dropwise. The reaction mixture was diluted with ethyl acetate (100 ml). The phases were separated. The aqueous phase was extracted with ethyl acetate (2×100 ml). The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (200 ml) and dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (50 g), using ethyl acetate/heptane (1:10) as eluent, to give 1.35 g of 1-bromo-5-phenylpentane. The reaction mixture was stirred for 16 h at room temprature It was cooled to 0° C The phases were separated The aqueous phase was extracted with ethyl acetate (2×100 ml) The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (200 ml) dried over magnesium sulfate The solvent was removed in vacuo The crude product was purified by flash chromatography on silica (50 g)

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

Procedure: A vigorously stirred solution of 5-phenylpentanol (10 g), sodium bromide (6.45 g) and TEMPO, 2,2,6,6-tetramethyl-1-piperidinyloxy, (0.095 g) in a mixture of ethyl acetate, toluene and water (258 ml, 7:7:1, v/v/v), at 0° C., was treated with aqueous sodium hypochlorite solution (571 ml, 0.35M) saturated with sodium bicarbonate (43.85 g) in five portions separated by 10 minute intervals. The reaction mixture was treated with ethanol (20 ml) then partitioned between water (500 ml) and ethyl acetate (500 ml). The aqueous layer was extracted twice with ethyl acetate (500 ml). The combined organic phases were washed with aqueous sodium thiosulphate (500 ml, 5%), then with water (200 ml), then with brine (200 ml), then dried over magnesium sulphate and then evaporated to give the title compound as an orange oil, which was used without further purification. NMR (CDCl3): δ1.65 (m,4H), 2.35 (m,2H), 2.60 (t,2H), 7.10-7.30 (m,5H), 9.75 (s,1H). separated by 10 minute intervals The reaction mixture was treated with ethanol (20 ml) then partitioned between water (500 ml) and ethyl acetate (500 ml) The aqueous layer was extracted twice with ethyl acetate (500 ml) The combined organic phases were washed with aqueous sodium thiosulphate (500 ml, 5%) with water (200 ml), then with brine (200 ml), then dried over magnesium sulphate evaporated

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

Procedure: 5-Phenyl-pentanol (40 g, 244 mmoles) in methylene chloride (80 ml) at 0° C. was added with triethylamine (39 ml, 28.34 g, 280 mmoles) and a solution of methyl-sulfonyl chloride (20.7 ml, 30.69 g, 268 mmoles) in methylene chloride (40 ml). The temperature was left to rise to the room value, then the mixture was poured into water and the organic phase was isolated, washed with water, anhydrified and concentrated to give 59.49 g of the title product (yield: 99%). The temperature was left the organic phase was isolated washed with water, anhydrified concentrated

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

Procedure: To a mixture of 5-phenylpentanol (3.7 mL), methyl 3-(4-hydroxyphenyl)propanoate (3.6 g), triphenylphosphine (5.77 g) and dichloromethane (200 mL) was added 1,1′-(azodicarbonyl)dipiperidine (5.55 g). The reaction mixture was stirred at room temperature for 4 days. Diethyl ether was added to the reaction mixture, which was filtered and the filtrate was concentrated. Hexane-diethyl ether (1:1) (200 mL) was added to the residue, which was filtered and the filtrate was concentrated. The obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=9:1→4:1) to give the title compound (6.16 g) having the following physical data. was filtered the filtrate was concentrated Hexane-diethyl ether (1:1) (200 mL) was added to the residue, which was filtered the filtrate was concentrated The obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=9:1→4:1)