1-bromoundecane

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

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Undecyltriphenylphosphonium bromide (16.3 g, prepared by heating 1-bromoundecane and triphenylphosphine together in refluxing xylene) is suspended in dry ether (400 ml) and the mixture is stirred under nitrogen whilst 1.7 M butyllithium in hexane (47.5 ml) is added from a syringe. The resulting bright red solution is cooled to 10° C. and treated dropwise with ethyl 5-oxopentanoate (7.25 g) in dry ether (50 ml). After 10 minutes, water (200 ml) is added and when the solid product has dissolved the ether layer is separated and the aqueous layer is washed with ether (3×100 ml). The combined ethereal solutions are dried over magnesium sulphate and the ether is evaporated. The residue is shaken with hexane (200 ml), and the mixture is cooled and filtered. The filtrate is concentrated to a volume of 100 ml and then cooled to allow crystallisation of the triphenylphosphine oxide. When this is complete, the mixture is filtered and the filtrate is evaporated to yield ethyl (Z)-hexadec-5-enoate in crude form as a yellow oil (10.1 g). is added from a syringe is separated the aqueous layer is washed with ether (3×100 ml) The combined ethereal solutions are dried over magnesium sulphate the ether is evaporated the mixture is cooled filtered The filtrate is concentrated to a volume of 100 ml cooled crystallisation of the triphenylphosphine oxide When this is complete, the mixture is filtered the filtrate is evaporated

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

Procedure: Undecanol (14 g), 48% aqueous hydrobromic acid (30 g) and concentrated sulphuric acid (5 ml) are heated together under reflux for 51/2 hours. After cooling, water is added and the organic layer is separated, washed with concentrated sulphuric acid (20 ml), brine (50 ml) and dilute aqueous sodium carbonate (50 ml), and is then dried over calcium chloride. Distillaion under vacuum gives 1-bromoundecane (12 g) as a yellow oil, b.p. 60°-70° C./0.1 mm. under reflux for 51/2 hours After cooling the organic layer is separated washed with concentrated sulphuric acid (20 ml), brine (50 ml) and dilute aqueous sodium carbonate (50 ml) is then dried over calcium chloride

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

Procedure: p-Aminobenzophenone (75 g.) is heated with undecyl bromide (200 g.) in dry hexamethyl phosphoramide (300 ml.) containing anhydrous potassium carbonate (90 g.) for 16 hours at 100° C. The solution is cooled to room temperature, filtered to remove solids, and the filtrate is diluted with cold water. The solid so obtained is collected and washed with water. Recrystallization from ethanol followed by dichloro methane provides the product of the Example. filtered to remove solids the filtrate is diluted with cold water The solid so obtained is collected washed with water Recrystallization from ethanol provides the product of the Example

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-hydroxy-5-methoxybenzaldehyde (10 g, 65.7 mmoles) in 100 ml of sieve-dried dimethylformamide was added freshly-pulverized potassium carbonate (10 g, 72.3 mmoles) and undecyl bromide (15 ml, 67.3 mmoles). The reaction mixture was stirred at 100° C. for 1 hour, cooled to room temperature and then poured into ice-cold water/hexane. The layers were separated and the organic extract was washed with ice-cold 5% sodium hydroxide solution, water and saturated sodium chloride solution. The organic layer was dried with anhydrous magnesium sulfate, treated with charcoal and concentrated in vacuo. The resulting yellow solid was recrystallized from hexane, to give 16.2 g (80%) of the product as a white solid. cooled to room temperature poured into ice-cold water/hexane The layers were separated the organic extract was washed with ice-cold 5% sodium hydroxide solution, water and saturated sodium chloride solution The organic layer was dried with anhydrous magnesium sulfate treated with charcoal concentrated in vacuo The resulting yellow solid was recrystallized from hexane

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

Procedure: A solution containing lithium diisopropylamide (0.1 mole) was prepared by treating a solution of diisopropylamine (14.1 ml, 0.1 mole) in tetrahydrofuran (200 ml) at 0° C. with n-butyl lithium (41.2 ml of a 2.43M solution, 0.1 mole), and stirring for 5 minutes. To this was added a solution of o-toluic acid (6.8 g, 0.05 mole) in tetrahydrofuran (50 ml). The ice bath was removed and the intense red solution was stirred for 30 minutes. This solution was slowly pipetted into a solution of undecylbromide (11.8 g, 0.05 mole) in tetrahydrofuran (50 ml) at -20° C. After the addition, the cooling bath was removed and the solution stirred for 30 minutes. A small amount of water was added and most of the tetrahydrofuran was removed under reduced pressure. The residue was poured into water, acidified with 3N hydrochloric acid and extracted with ether. The ether was dried, evaporated and the residue was recrystallized from acetonitrile, then from hexane, to give the product. was prepared The ice bath was removed the intense red solution was stirred for 30 minutes After the addition the cooling bath was removed the solution stirred for 30 minutes A small amount of water was added and most of the tetrahydrofuran was removed under reduced pressure The residue was poured into water extracted with ether The ether was dried evaporated the residue was recrystallized from acetonitrile from hexane, to give the product

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of salicylaldehyde (10.15 mmoles), undecylbromide (10.3 mmoles) and potassium carbonate (11.7 mmoles) in dimethylformamide (10 ml) is heated to 100° C. for 1 hour and then is cooled. The reaction mixture is taken up in hexane and is washed with 5 percent sodium hydroxide and brine. After treatment with anhydrous magnesium sulfate and charcoal, the volatiles are removed under vacuum and the residue is purified by flash chromatography to give the desired product. is cooled is washed with 5 percent sodium hydroxide and brine After treatment with anhydrous magnesium sulfate and charcoal, the volatiles are removed under vacuum the residue is purified by flash chromatography

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

Procedure: To a stirred suspension of sodium hydride (10.0 mmoles), which was prewashed with petroleum ether, in sieve dried dimethylformamide (10 ml) was added dropwise a solution of salicylaldehyde (10.1 mmoles) in dimethylformamide (1 ml). To the reaction mixture was then added undecyl bromide (10.0 mmoles) and the mixture stirred for 16 hours at ambient temperature under nitrogen. The reaction mixture was taken up in hexane (50 ml) and washed with 10 percent sodium hydroxide (2×50 ml) and saturated sodium chloride (50 ml). The organic phase was dried over anhydrous magnesium sulfate and charcoal. Evaporation of the volatiles yielded a colorless liquid which was purified by flash chromatography over silica gel with 2 percent ethyl acetate in hexane as eluant to afford the desired product as an oil. washed with 10 percent sodium hydroxide (2×50 ml) and saturated sodium chloride (50 ml) The organic phase was dried over anhydrous magnesium sulfate and charcoal Evaporation of the volatiles yielded a colorless liquid which was purified by flash chromatography over silica gel with 2 percent ethyl acetate in hexane as eluant

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

Procedure: A solution of 3-[2-(4-benzyloxyphenyl)-5-methyl-1H-pyrrol-1-yl]phenol (1.80 g, 5.07 mmol), 1-bromoundecane (1.58 ml, 7.60 mmol) and potassium carbonate (1.05 g, 7.06 mmol) in DMF (15 ml) was stirred at 80° C. for 12 hours. The reaction solution was poured into water and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over magnesium sulfate anhydride, and solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the object compound as an oily substance. 1.90 g (yield: 75.7%) the mixture was extracted with ethyl acetate The extract was washed with water dried over magnesium sulfate anhydride, and solvent was removed under reduced pressure The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the object compound as an oily substance

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

Procedure: A solution of 4-[2-(4-benzyloxyphenyl)-5-methyl-1H-pyrrol-1-yl]phenol (1.50 g, 4.22 mmol), 1-bromoundecane (1.31 ml, 6.33 mmol) and potassium carbonate (874 mg, 6.33 mmol) in DMF (15 ml) was stirred at 80° C. for 4 hours. The reaction solution was poured into water and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate anhydride and solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the object compound as an oily substance. 1.78 g (yield: 85.2%) the mixture was extracted with ethyl acetate The extract was washed with water dried over magnesium sulfate anhydride and solvent was removed under reduced pressure The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the object compound as an oily substance

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

Procedure: A solution of 4-[2-(4-benzyloxyphenyl)-5-methyl-1H-pyrrol-1-yl]phenol (1.50 g, 4.22 mmol), 1-bromoundecane (1.31 ml, 6.33 mmol) and potassium carbonate (874 mg, 6.33 mmol) in DMF (15 ml) was stirred at 80° C. for 4 hours. The reaction solution was poured into water and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate anhydride and solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the object compound as an oily substance. 1.78 g (yield: 85.2%) the mixture was extracted with ethyl acetate The extract was washed with water dried over magnesium sulfate anhydride and solvent was removed under reduced pressure The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the object compound as an oily substance

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

Procedure: A solution of 4-{2-[2-(4-benzyloxyphenyl)-5-methyl-1H-pyrrol-1-yl]ethyl}phenol (1.50 g, 3.91 mmol), 1-bromoundecane (1.31 ml, 5.87 mmol) and potassium carbonate (811 mg, 5.87 mmol) in DMF (15 ml) was stirred at 80° C. for 4 hours. The reaction solution was poured into water and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over magnesium sulfate anhydride, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the object compound as an oily substance. 1.80 g (yield: 85.7%) the mixture was extracted with ethyl acetate The extract was washed with water dried over magnesium sulfate anhydride the solvent was removed under reduced pressure The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the object compound as an oily substance