1-[2-(2-chloroethoxy)ethoxy]-2-methoxyethane

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:-7.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 7.69 g of butyllithium dissolved in 48 ml of hexane was slowly added during 5 minutes into 20.0 g of fluorene dissolved in 150 ml of anhydrous tetrahydrofuran at -50° C. under nitrogen protection. The mixture was stirred at -30 to 15° C. for 1 hour before it was cooled again to -40 to -50° C. Then, 23.17 g of 2-ethylhexyl bromide was added in 5 minutes. The mixture was subsequently stirred for 2 hours while the temperature was gradually increased to 22° C. The main product in the solution was 9-(2-ethylhexyl)-fluorene as detected by GC-MS. This solution was then cooled to -50° C., and 7.7 g of butyllithium dissolved in 48 ml of hexane was slowly added in 5 minutes under nitrogen protection. The mixture was stirred at -30~15° C. for 1 hour before it was cooled again to -40 to -50° C. Then, 23.75 g of 1-(2-chloroethoxy)-2-(2-methoxyethoxy)-ethane was added in 5 minutes. The mixture was subsequently stirred for 15 hours at 22° C., dispersed in water, and extracted with ether. The etheral solution was washed with water and brine, dried with magnesium sulfate, and evaporated. The residue was distilled to collect 45.5 g (89%) of colorless liquid at 190° C./0.12 mm Hg. MS (m/z): 424 (M+), 277, 205, 191, 178, 165, 133, 103, 59. was cooled again to -40 to -50° C The mixture was subsequently stirred for 2 hours while the temperature was gradually increased to 22° C This solution was then cooled to -50° C. was slowly added in 5 minutes under nitrogen protection The mixture was stirred at -30~15° C. for 1 hour before it was cooled again to -40 to -50° C The mixture was subsequently stirred for 15 hours at 22° C. extracted with ether The etheral solution was washed with water and brine dried with magnesium sulfate evaporated The residue was distilled to collect 45.5 g (89%) of colorless liquid at 190° C./0.12 mm Hg

Conditions: temp:-7.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 7.69 g of butyllithium dissolved in 48 ml of hexane was slowly added during 5 minutes into 20.0 g of fluorene dissolved in 150 ml of anhydrous tetrahydrofuran at -50° C. under nitrogen protection. The mixture was stirred at -30 to 15° C. for 1 hour before it was cooled again to -40 to -50° C. Then, 23.17 g of 2-ethylhexyl bromide was added in 5 minutes. The mixture was subsequently stirred for 2 hours while the temperature was gradually increased to 22° C. The main product in the solution was 9-(2-ethylhexyl)-fluorene as detected by GC-MS. This solution was then cooled to -50° C., and 7.7 g of butyllithium dissolved in 48 ml of hexane was slowly added in 5 minutes under nitrogen protection. The mixture was stirred at -30~15° C. for 1 hour before it was cooled again to -40 to -50° C. Then, 23.75 g of 1-(2-chloroethoxy)-2-(2-methoxyethoxy)-ethane was added in 5 minutes. The mixture was subsequently stirred for 15 hours at 22° C., dispersed in water, and extracted with ether. The etheral solution was washed with water and brine, dried with magnesium sulfate, and evaporated. The residue was distilled to collect 45.5 g (89%) of colorless liquid at 190° C./0.12 mm Hg. MS (m/z): 424 (M+), 277, 205, 191, 178, 165, 133, 103, 59. was cooled again to -40 to -50° C The mixture was subsequently stirred for 2 hours while the temperature was gradually increased to 22° C This solution was then cooled to -50° C. was slowly added in 5 minutes under nitrogen protection The mixture was stirred at -30~15° C. for 1 hour before it was cooled again to -40 to -50° C The mixture was subsequently stirred for 15 hours at 22° C. extracted with ether The etheral solution was washed with water and brine dried with magnesium sulfate evaporated The residue was distilled to collect 45.5 g (89%) of colorless liquid at 190° C./0.12 mm Hg

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

Procedure: 1-[2-[2-(2-Methoxyethoxy)ethoxy]ethyl]-2-methyl-1H-benzimidazole was synthesized as in Synthesis Example 1 except that an equimolar amount of 2-methylbenzimidazole was used instead of benzimidazole and an equimolar amount of 2-chloroethyl 2-(2-methoxyethoxy)ethyl ether was used instead of 2-chloroethyl methyl ether. Yield 82%.

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

Procedure: 1-[2-[2-(2-Methoxyethoxy)ethoxy]ethyl]-2-methyl-1H-benzimidazole was synthesized as in Synthesis Example 1 except that an equimolar amount of 2-methylbenzimidazole was used instead of benzimidazole and an equimolar amount of 2-chloroethyl 2-(2-methoxyethoxy)ethyl ether was used instead of 2-chloroethyl methyl ether. Yield 82%.

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

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

Procedure: Under argon, 630 mg (27.4 mmol) of sodium are added to 10 ml of diethylene glycol and the mixture is heated for one hour at 100° C. At that temperature, 5 g (27.4 mmol) of 3,6,9-trioxadecyl chloride are added dropwise thereto using a syringe. The mixture is stirred overnight at 100° C. to complete the reaction. After cooling, the reaction solution is taken up in CH2Cl2, washed with water and brine and dried over Na2SO4. Removal of the solvent yields 3,6,9,12,15-pentaoxa-hexadecanol in the form of an oil (Liebigs Ann. Chem. 1980, 858); NMR(CDCl3): 3.8-3.5 (m,20H); 3.75 (s,3H). the reaction After cooling washed with water and brine dried over Na2SO4 Removal of the solvent

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

Procedure: Under argon, 630 mg (27.4 mmol) of sodium are added to 10 ml of diethylene glycol and the mixture is heated for one hour at 100° C. At that temperature, 5 g (27.4 mmol) of 3,6,9-trioxadecyl chloride are added dropwise thereto using a syringe. The mixture is stirred overnight at 100° C. to complete the reaction. After cooling, the reaction solution is taken up in CH2Cl2, washed with water and brine and dried over Na2SO4. Removal of the solvent yields 3,6,9,12,15-pentaoxa-hexadecanol in the form of an oil (Liebigs Ann. Chem. 1980, 858); NMR(CDCl3): 3.8-3.5 (m,20H); 3.75 (s,3H). the reaction After cooling washed with water and brine dried over Na2SO4 Removal of the solvent

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

Procedure: 19.02 g (0.116 mol) of triethylene glycol monomethyl ether and 21 ml (20.54 g=0.26 mol) of pyridine in 110 ml of benzene are heated to reflux, and 19 ml (31 g=0.26 mol) of thionyl chloride are added dropwise thereto. The mixture is boiled under reflux for a further 20 hours. When the reaction solution has cooled, a mixture consisting of 5 ml of concentrated hydrochloric acid and 20 ml of water is added thereto, with stirring. The organic phase is separated off and washed repeatedly with water and brine. The solvent is extensively distilled off using a Vigreux column and the residue is purified on silica gel in hexane/ethyl acetate (4:1). The product-containing fractions are concentrated and the residue is distilled, yielding 3,6,9-trioxadecyl chloride (J. Am. Chem. Soc. 89, 7017 (1967)); b.p. 76° C./2 mbar, NMR (CDCl3): 3.8-3.5 (m,12H); 3.37 (s,3H). to reflux under reflux for a further 20 hours When the reaction solution has cooled is added The organic phase is separated off washed repeatedly with water and brine The solvent is extensively distilled off the residue is purified on silica gel in hexane/ethyl acetate (4:1) The product-containing fractions are concentrated the residue is distilled

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

Procedure: 19.02 g (0.116 mol) of triethylene glycol monomethyl ether and 21 ml (20.54 g=0.26 mol) of pyridine in 110 ml of benzene are heated to reflux, and 19 ml (31 g=0.26 mol) of thionyl chloride are added dropwise thereto. The mixture is boiled under reflux for a further 20 hours. When the reaction solution has cooled, a mixture consisting of 5 ml of concentrated hydrochloric acid and 20 ml of water is added thereto, with stirring. The organic phase is separated off and washed repeatedly with water and brine. The solvent is extensively distilled off using a Vigreux column and the residue is purified on silica gel in hexane/ethyl acetate (4:1). The product-containing fractions are concentrated and the residue is distilled, yielding 3,6,9-trioxadecyl chloride (J. Am. Chem. Soc. 89, 7017 (1967)); b.p. 76° C./2 mbar, NMR (CDCl3): 3.8-3.5 (m,12H); 3.37 (s,3H). to reflux under reflux for a further 20 hours When the reaction solution has cooled is added The organic phase is separated off washed repeatedly with water and brine The solvent is extensively distilled off the residue is purified on silica gel in hexane/ethyl acetate (4:1) The product-containing fractions are concentrated the residue is distilled