1-bromoicosane

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

Procedure: Diethyl 2-acetamidomalonate (3.0 g) was dissolved in 50 ml of dry ethanol and 1.3 g of sodium ethoxide was added thereto. A solution of 6.0 g of icosyl bromide in 20 ml of dry ethanol was added thereto while stirring at room temperature. The inside of the reaction vessel was displaced with nitrogen and the mixture was refluxed for about 15 hours. The mixture was neutralized with a 1N aqueous hydrochloric acid solution and concentrated. The concentrate was purified by silica gel column chromatography to give 4 g of diethyl 2-acetamido-2-icosylmalonate. the mixture was refluxed for about 15 hours concentrated The concentrate was purified by silica gel column chromatography

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

Procedure: Diethyl 2-acetamidomalonate (3.0 g) was dissolved in 50 ml of dry ethanol and 1.3 g of sodium ethoxide was added thereto. A solution of 6.0 g of icosyl bromide in 20 ml of dry ethanol was added thereto while stirring at room temperature. The inside of the reaction vessel was displaced with nitrogen and the mixture was refluxed for about 15 hours. The mixture was neutralized with a 1N aqueous hydrochloric acid solution and concentrated. The concentrate was purified by silica gel column chromatography to give 4 g of diethyl 2-acetamido-2-icosylmalonate. the mixture was refluxed for about 15 hours concentrated The concentrate was purified by silica gel column chromatography

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

Procedure: In accordance with (1--1) and (1-2) of Example 1, using eicosanyl bromide and undecenylmagnesium bromide as the raw material, a similar reaction was carried out to obtain hentriacontane as the intermediate product and then by another reaction 1,1,1-trichlorodotriacontane was obtained. One gram of the thus obtained, 1,1,1-trichlorodotriacontane dissolved in 6 ml of n-butyl alcohol was placed in a 50-ml conical flask and 1.4 ml of distilled water and 2.5 g of potassium hydroxide were added to the solution in the flask. The mixture was heated to a temperature of 60° C. to make reaction for 30 hours under agitation. Then, iced water was added to the reaction mixture to cool the mixture, and after neutralizing with an aqueous dilute hydrochloric acid, the separated precipitate was collected by filtration and dried to obtain 0.82 g of the product. After recrystallizing from benzene, 0.52 g of dotriacontanoic acid melting at 95.5° C. was obtained with a yield of 60%. a similar reaction

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

Procedure: Diethyl 2-acetamidomalonate (3.0 g) was dissolved in 50 ml of dry ethanol and 1.3 g of sodium ethoxide was added thereto. A solution of 6.0 g of icosyl bromide in 20 ml of dry ethanol was added thereto while stirring at room temperature. The inside of the reaction vessel was displaced with nitrogen and the mixture was refluxed for about 15 hours. The mixture was neutralized with a 1 N aqueous hydrochloric acid solution and concentrated. The concentrate was purified by silica gel column chromatography to give 4 g of diethyl 2-acetamido-2-icosylmalonate. the mixture was refluxed for about 15 hours concentrated The concentrate was purified by silica gel column chromatography

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

Procedure: Diethyl 2-acetamidomalonate (3.0 g) was dissolved in 50 ml of dry ethanol and 1.3 g of sodium ethoxide was added thereto. A solution of 6.0 g of icosyl bromide in 20 ml of dry ethanol was added thereto while stirring at room temperature. The inside of the reaction vessel was displaced with nitrogen and the mixture was refluxed for about 15 hours. The mixture was neutralized with a 1 N aqueous hydrochloric acid solution and concentrated. The concentrate was purified by silica gel column chromatography to give 4 g of diethyl 2-acetamido-2-icosylmalonate. the mixture was refluxed for about 15 hours concentrated The concentrate was purified by silica gel column chromatography

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.53 g of anhydrous potassium carbonate are added to a solution of 2.5 g of 3,6-diaminoacridine hydrochloride and 2.95 g of 1-eicosyl bromide in 20 ml of N,N'-dimethylethyleneurea, and the mixture is stirred at 50° C. for 86 hours. The cooled reaction mixture is subsequently poured into water, and the orange-brown suspension is extracted with methylene chloride. The organic phase is washed with water and dried over sodium sulfate. After evaporation, 2N HCl is added to the brown oil. The red precipitate formed is filtered off, washed with water and then dried in a high vacuum. The resultant red-brown crystals are taken up in methylene chloride/methanol (10:1) and chromatographed on silica gel. After evaporation, the residue is taken up in diethyl ether/methanol (10:1) and re-chromatographed on silica gel, giving the title compound as red crystals, absorption spectrum (ethanol): λmax =472 nm; ε=42 200. The cooled reaction mixture the orange-brown suspension is extracted with methylene chloride The organic phase is washed with water dried over sodium sulfate After evaporation, 2N HCl is added to the brown oil The red precipitate formed is filtered off washed with water dried in a high vacuum chromatographed on silica gel After evaporation re-chromatographed on silica gel giving the title compound as red crystals, absorption spectrum (ethanol)

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

Procedure: 5 g (0.0198 mol) of 11-tetrahydropyranyloxyundecyne of Example 7 were placed in a mixture of 50 ml of THF and 25 ml of hexamethylphosphoric triamide under an argon atmosphere. At -60° C., 12.4 ml (0.0198 mol) of n-butyllithium in hexane were added dropwise. After 30 min at -60° C., a solution of 9.0 g (0.0248 mol) of 1-bromoeicosane in 25 ml of THF was added dropwise at -60° C. The mixture was left to warm up to room temperature. After 18 h at room temperature, it was poured into 25% aqueous NaH2PO4 solution and extracted with n-heptane (3×). The combined organic phases were dried (Na2SO4) and the solvent was removed. Flash chromatography on silica gel (n-heptane/ethyl acetate =15:1) gave 6.5 g (61.3% of theory) of 1-tetrahydropyranyloxy-hentriacont-10-yne. The mixture was left After 18 h at room temperature extracted with n-heptane (3×) The combined organic phases were dried (Na2SO4) the solvent was removed

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

Procedure: 8.6 ml (76.08 mmol) of (R)-(−)-2,2-dimethyl-1,3-dioxolane-4-methanol, 15 grams of powdered potassium hydroxide and 27.5 grams (76.08 mmol) of 1-bromoeicosane were stirred in 150 ml benzene and refluxed for 6 hours, while removing the water formed by azeotropic distillation. The volume of the solvent was gradually reduced to about 70 ml. The reaction mixture was then cooled to room temperature and 150 ml of water was added. The reaction mixture was then extracted thrice with 150 ml diethyl ether, the combined organic phase was washed with 100 ml water, and the solvent was then removed under reduced pressure. The obtained residue was dissolved in 105 ml of a 90:10:5 (v/v) methanol:water:concentrated hydrochloric acid mixture, and the resulting solution was refluxed until the solution became clear. The solution was then cooled to room temperature and 100 ml water was added. The product was extracted with 150 ml chloroform, washed consecutively with 150 ml water, 150 ml saturated aqueous solution of sodium carbonate, and again with 150 ml water. The solvent was then removed under reduced pressure and the product was crystallized from 200 ml hexane, yielding 21.0 grams of pure 1-eicosanyl-sn-glycerol, which was dried in a desiccator under reduced pressure with phosphorus oxide. The yield was 81.5%. refluxed for 6 hours while removing the water formed by azeotropic distillation The reaction mixture was then extracted thrice with 150 ml diethyl ether the combined organic phase was washed with 100 ml water the solvent was then removed under reduced pressure The obtained residue was dissolved in 105 ml of a 90:10:5 (v/v) methanol water:concentrated hydrochloric acid mixture, and the resulting solution was refluxed until the solution The solution was then cooled to room temperature 100 ml water was added The product was extracted with 150 ml chloroform washed consecutively with 150 ml water, 150 ml saturated aqueous solution of sodium carbonate The solvent was then removed under reduced pressure the product was crystallized from 200 ml hexane

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

Procedure: Diethyl 2-acetamidomalonate (3.0 g) was dissolved in 50 ml of dry ethanol and 1.3 g of sodium ethoxide was added thereto. A solution of 6.0 g of icosyl bromide in 20 ml of dry ethanol was added thereto while stirring at room temperature. The inside of the reaction vessel was displaced with nitrogen and the mixture was refluxed for about 15 hours. The mixture was neutralized with a 1N aqueous hydrochloric acid solution and concentrated. The concentrate was purified by silica gel column chromatography to give 4 g of diethyl 2-acetamido-2-icosylmalonate. the mixture was refluxed for about 15 hours concentrated The concentrate was purified by silica gel column chromatography

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

Procedure: Diethyl 2-acetamidomalonate (3.0 g) was dissolved in 50 ml of dry ethanol and 1.3 g of sodium ethoxide was added thereto. A solution of 6.0 g of icosyl bromide in 20 ml of dry ethanol was added thereto while stirring at room temperature. The inside of the reaction vessel was displaced with nitrogen and the mixture was refluxed for about 15 hours. The mixture was neutralized with a 1N aqueous hydrochloric acid solution and concentrated. The concentrate was purified by silica gel column chromatography to give 4 g of diethyl 2-acetamido-2-icosylmalonate. the mixture was refluxed for about 15 hours concentrated The concentrate was purified by silica gel column chromatography

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

Procedure: In accordance with (1--1) and (1-2) of Example 1, using eicosanyl bromide and undecenylmagnesium bromide as the raw material, a similar reaction was carried out to obtain hentriacontane as the intermediate product and then by another reaction 1,1,1-trichlorodotriacontane was obtained. One gram of the thus obtained, 1,1,1-trichlorodotriacontane dissolved in 6 ml of n-butyl alcohol was placed in a 50-ml conical flask and 1.4 ml of distilled water and 2.5 g of potassium hydroxide were added to the solution in the flask. The mixture was heated to a temperature of 60° C. to make reaction for 30 hours under agitation. Then, iced water was added to the reaction mixture to cool the mixture, and after neutralizing with an aqueous dilute hydrochloric acid, the separated precipitate was collected by filtration and dried to obtain 0.82 g of the product. After recrystallizing from benzene, 0.52 g of dotriacontanoic acid melting at 95.5° C. was obtained with a yield of 60%. a similar reaction

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

Procedure: Diethyl 2-acetamidomalonate (3.0 g) was dissolved in 50 ml of dry ethanol and 1.3 g of sodium ethoxide was added thereto. A solution of 6.0 g of icosyl bromide in 20 ml of dry ethanol was added thereto while stirring at room temperature. The inside of the reaction vessel was displaced with nitrogen and the mixture was refluxed for about 15 hours. The mixture was neutralized with a 1 N aqueous hydrochloric acid solution and concentrated. The concentrate was purified by silica gel column chromatography to give 4 g of diethyl 2-acetamido-2-icosylmalonate. the mixture was refluxed for about 15 hours concentrated The concentrate was purified by silica gel column chromatography