15-bromopentadecan-1-ol

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

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

Procedure: Diol 22 (4.70 g, 19.2 mmol) was dissolved in cyclohexane (50 mL) and 48% HBr (2.4 mL, 21.2 mmol, 1.1 eq.) was added under vigorous stirring. The mixture was refluxed overnight. After cooling to r.t., saturated sodium bicarbonate solution (100 mL) was added and the phases were separated. The aqueous phase was extracted with dichloromethane (3×50 mL). The combined organic layers were dried over MgSO4. After evaporation of the solvent the product was purified by column chromatography (silica gel, 27×4 cm, cyclohexane/ethyl acetate, 4:1→100% ethyl acetate) and isolated as a white solid. Yield: 3.39 g (58%). Traces of 1,15-dibromopentadecane were also found. The mixture was refluxed overnight the phases were separated The aqueous phase was extracted with dichloromethane (3×50 mL) The combined organic layers were dried over MgSO4 After evaporation of the solvent the product was purified by column chromatography (silica gel, 27×4 cm, cyclohexane/ethyl acetate, 4:1→100% ethyl acetate) isolated as a white solid

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

Procedure: Diol 22 (4.70 g, 19.2 mmol) was dissolved in cyclohexane (50 mL) and 48% HBr (2.4 mL, 21.2 mmol, 1.1 eq.) was added under vigorous stirring. The mixture was refluxed overnight. After cooling to r.t., saturated sodium bicarbonate solution (100 mL) was added and the phases were separated. The aqueous phase was extracted with dichloromethane (3×50 mL). The combined organic layers were dried over MgSO4. After evaporation of the solvent the product was purified by column chromatography (silica gel, 27×4 cm, cyclohexane/ethyl acetate, 4:1→100% ethyl acetate) and isolated as a white solid. Yield: 3.39 g (58%). Traces of 1,15-dibromopentadecane were also found. The mixture was refluxed overnight the phases were separated The aqueous phase was extracted with dichloromethane (3×50 mL) The combined organic layers were dried over MgSO4 After evaporation of the solvent the product was purified by column chromatography (silica gel, 27×4 cm, cyclohexane/ethyl acetate, 4:1→100% ethyl acetate) isolated as a white solid

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

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

Procedure: 15-Bromo-pentadecan-1-ol (2.3 g, 7.49 mmol) dissolved in methylene chloride (23 mL) was mixed with trimethylamine (2.1 mL, 14.98 mmol), t-butyldimethylsilyl chloride (2.03 g, 13.48 mmol), and dimethylaminopyridine (457.6 mg, 3.74 mmol). The mixture was stirred for one hour at room temperature. Subsequently, aqueous saturated ammonium chloride solution was added to the reaction mixture for separation into a methylene chloride layer (200 mL) and an aqueous layer (200 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by means of silica gel column flash chromatography (hexane/ethyl acetate=99/1), to thereby afford 2.98 g (7.07 mmol) of 15-bromo-1-(t-butyldimethylsiloxy)pentadecane. The organic layer was dried over magnesium sulfate filtered concentrated under reduced pressure The crude product was purified by means of silica gel column flash chromatography (hexane/ethyl acetate=99/1)

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

Procedure: Diol 22 (4.70 g, 19.2 mmol) was dissolved in cyclohexane (50 mL) and 48% HBr (2.4 mL, 21.2 mmol, 1.1 eq.) was added under vigorous stirring. The mixture was refluxed overnight. After cooling to r.t., saturated sodium bicarbonate solution (100 mL) was added and the phases were separated. The aqueous phase was extracted with dichloromethane (3×50 mL). The combined organic layers were dried over MgSO4. After evaporation of the solvent the product was purified by column chromatography (silica gel, 27×4 cm, cyclohexane/ethyl acetate, 4:1→100% ethyl acetate) and isolated as a white solid. Yield: 3.39 g (58%). Traces of 1,15-dibromopentadecane were also found. The mixture was refluxed overnight the phases were separated The aqueous phase was extracted with dichloromethane (3×50 mL) The combined organic layers were dried over MgSO4 After evaporation of the solvent the product was purified by column chromatography (silica gel, 27×4 cm, cyclohexane/ethyl acetate, 4:1→100% ethyl acetate) isolated as a white solid

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