1,22-Docosanediol

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

Procedure: 1,22-Docosanediol 1 (2.00 g, 5.84 mmol) and imidazole (0.817 g, 12.0 mmol) were placed in each of two nitrogen-purged 150 mL three-necked flasks fitted with a thermometer and magnetic stir bar. The flasks were resealed and purged with nitrogen. Dimethylformamide (40 mL) was added to each flask and the cloudy mixtures were heated until they became homogenous at 63° C. tert-Butyldimethylsilyl chloride (0.904 g, 6.00 mmol, in 10 mL DMF) was slowly added to the reaction mixture (the transfer was aided with an additional 5 mL of DMF) and the mixture was allowed to react for 24 hours at 60°-65° C. The solutions were cooled down to room temperature and filtered to recover starting material using water (25 mL) to aid in transfer. The filtrate was diluted with water (300 mL) and extracted with methylene chloride (500 mL). The organic layer was dried (Na2SO4) and concentrated. A very low mass balance led to the discovery that much of the desired material was contained in the recovered solid that had been previously filtered off. None of the desired compound was found in the aqueous wash by TLC. The recovered solid was suspended in methylene chloride (100 mL), stirred, and refiltered. The filtrate was combined with the previously isolated material and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 10% ethyl acetate/hexane). Concentration of the desired fractions using acetone to reduce violent bumping yielded the desired material 2 as a white solid (2.22 g, 46.7%). purged 150 mL three-necked flasks fitted with a thermometer and magnetic stir bar purged with nitrogen Dimethylformamide (40 mL) was added to each flask the cloudy mixtures were heated until they became homogenous at 63° C. was slowly added to the reaction mixture (the transfer to react for 24 hours at 60°-65° C filtered to recover The filtrate was diluted with water (300 mL) extracted with methylene chloride (500 mL) The organic layer was dried (Na2SO4) concentrated had been previously filtered off aqueous wash by TLC concentrated in vacuo The crude material was purified by flash chromatography (silica gel, 10% ethyl acetate/hexane)

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

Procedure: 1,22-Docosanediol 1 (2.00 g, 5.84 mmol) and imidazole (0.817 g, 12.0 mmol) were placed in each of two nitrogen-purged 150 mL three-necked flasks fitted with a thermometer and magnetic stir bar. The flasks were resealed and purged with nitrogen. Dimethylformamide (40 mL) was added to each flask and the cloudy mixtures were heated until they became homogenous at 63° C. tert-Butyldimethylsilyl chloride (0.904 g, 6.00 mmol, in 10 mL DMF) was slowly added to the reaction mixture (the transfer was aided with an additional 5 mL of DMF) and the mixture was allowed to react for 24 hours at 60°-65° C. The solutions were cooled down to room temperature and filtered to recover starting material using water (25 mL) to aid in transfer. The filtrate was diluted with water (300 mL) and extracted with methylene chloride (500 mL). The organic layer was dried (Na2SO4) and concentrated. A very low mass balance led to the discovery that much of the desired material was contained in the recovered solid that had been previously filtered off. None of the desired compound was found in the aqueous wash by TLC. The recovered solid was suspended in methylene chloride (100 mL), stirred, and refiltered. The filtrate was combined with the previously isolated material and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 10% ethyl acetate/hexane). Concentration of the desired fractions using acetone to reduce violent bumping yielded the desired material 2 as a white solid (2.22 g, 46.7%). purged 150 mL three-necked flasks fitted with a thermometer and magnetic stir bar purged with nitrogen Dimethylformamide (40 mL) was added to each flask the cloudy mixtures were heated until they became homogenous at 63° C. was slowly added to the reaction mixture (the transfer to react for 24 hours at 60°-65° C filtered to recover The filtrate was diluted with water (300 mL) extracted with methylene chloride (500 mL) The organic layer was dried (Na2SO4) concentrated had been previously filtered off aqueous wash by TLC concentrated in vacuo The crude material was purified by flash chromatography (silica gel, 10% ethyl acetate/hexane)