2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethanol

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

Procedure: To the product of Example 200 (200 mg, 0.00033 mole) in DMA (1.5 mL) was added carbonyldiimidazole (67 mg, 0.00041 mole). The reaction was stirred at room temperature for 1 hour. Tetraethyleneglycol (214 mg, 0.0011 mole) was then added and the reaction mixture was stirred overnight at 60° C. The reaction was cooled to room temperature and the product was isolated by RPHPLC to yield the title compound (120 mg after lyophilization) as a hygroscopic white solid. MS and NMR were consistent with the desired structure. the reaction mixture was stirred overnight at 60° C The reaction was cooled to room temperature the product was isolated by RPHPLC

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium t-butoxide (Aldrich, 95%, 39.0 g) was added to a solution of tetraethylene glycol (Aldrich, 412.7 g) and methyl hexaethylene glycol chloride from above (95.8 g) at 18° C. over a 25 min period (ice/acetone bath). The reaction mixture was then stirred at 120° C. overnight. The pH was adjusted to 7 by the addition of hydrochloric acid (12 N, 11.7 ml), and volatiles were removed (64 Pa (0.48 Torr), up to 185° C.). The residual dark oil was diluted with toluene (250 ml), and treated with calcium chloride (38.1 g). After stirring for 18 h, the mixture was filtered through Celite™ and concentrated to a dark oil (102 g), which was fractionally distilled to provide decaethylene glycol monomethyl ether as an amber oil (64.4 g, 45%). were removed (64 Pa (0.48 Torr) up to 185° C. The residual dark oil was diluted with toluene (250 ml) treated with calcium chloride (38.1 g) After stirring for 18 h the mixture was filtered through Celite™ concentrated to a dark oil (102 g), which was fractionally distilled

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium t-butoxide (Aldrich, 95%, 39.0 g) was added to a solution of tetraethylene glycol (Aldrich, 412.7 g) and methyl hexaethylene glycol chloride from above (95.8 g) at 18° C. over a 25 min period (ice/acetone bath). The reaction mixture was then stirred at 120° C. overnight. The pH was adjusted to 7 by the addition of hydrochloric acid (12 N, 11.7 ml), and volatiles were removed (64 Pa (0.48 Torr), up to 185° C.). The residual dark oil was diluted with toluene (250 ml), and treated with calcium chloride (38.1 g). After stirring for 18 h, the mixture was filtered through Celite™ and concentrated to a dark oil (102 g), which was fractionally distilled to provide decaethylene glycol monomethyl ether as an amber oil (64.4 g, 45%). were removed (64 Pa (0.48 Torr) up to 185° C. The residual dark oil was diluted with toluene (250 ml) treated with calcium chloride (38.1 g) After stirring for 18 h the mixture was filtered through Celite™ concentrated to a dark oil (102 g), which was fractionally distilled

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

Procedure: Dissolve one equivalet of sodium in at least 5 equivalents of tetraethylene glycol and then add one equivalent of triethylene glycol monobenzenesulfonate. Heat the resulting solution at 100° to 150° C. until the elimination of sodium benzene sulfontate is substantially complete. Remove the insoluble sulfonate salt by filtration and fractionally distill the resultiing product in vacuo to obtain heptaethylene glycol as the higher boiling fraction. Remove the insoluble sulfonate salt by filtration fractionally distill the resultiing product in vacuo

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

Procedure: Dissolve one equivalet of sodium in at least 5 equivalents of tetraethylene glycol and then add one equivalent of triethylene glycol monobenzenesulfonate. Heat the resulting solution at 100° to 150° C. until the elimination of sodium benzene sulfontate is substantially complete. Remove the insoluble sulfonate salt by filtration and fractionally distill the resultiing product in vacuo to obtain heptaethylene glycol as the higher boiling fraction. Remove the insoluble sulfonate salt by filtration fractionally distill the resultiing product in vacuo

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

Procedure: 300 g. of tetraethylene glycol and 100 g. of anhydrous pyridine are slowly added to 727 g. of phosphorus tribromide, while agitating and cooling the mixture. After cooling to room temperature, the mixture is poured on to ice and the organic phase is decanted, washed with water and dilute hydrochloric acid and dried over sodium sulphate. After distillation under vacuum (123° C.-125° C. and 0.4 mm. Hg) the title comound is obtained. cooling the mixture the mixture is poured on to ice the organic phase is decanted washed with water and dilute hydrochloric acid dried over sodium sulphate After distillation under vacuum (123° C.-125° C. and 0.4 mm. Hg) the title comound is obtained

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

Procedure: 300 g. of tetraethylene glycol and 100 g. of anhydrous pyridine are slowly added to 727 g. of phosphorus tribromide, while agitating and cooling the mixture. After cooling to room temperature, the mixture is poured on to ice and the organic phase is decanted, washed with water and dilute hydrochloric acid and dried over sodium sulphate. After distillation under vacuum (123° C.-125° C. and 0.4 mm. Hg) the title comound is obtained. cooling the mixture the mixture is poured on to ice the organic phase is decanted washed with water and dilute hydrochloric acid dried over sodium sulphate After distillation under vacuum (123° C.-125° C. and 0.4 mm. Hg) the title comound is obtained

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

Procedure: 18.16 g (128.7 mmol) of 4-fluoronitrobenzene is added to 100 g (515.0 mmol) of tetraethylene glycol, 73 g (1300 mmol) of finely powdered potassium hydroxide and 500 mg of tetrabutylammonium hydrogen sulfate in 500 ml of toluene at 0° C., and it is stirred overnight at room temperature. 1000 ml of saturated common salt solution is; added, the organic phase is separated and it is dried on magnesium sulfate. It is evaporated to dryness in a vacuum, and the residue is chromatographed in silica gel (mobile solvent: methylene chloride/isopropanol=15:1). added the organic phase is separated it is dried on magnesium sulfate It is evaporated to dryness in a vacuum the residue is chromatographed in silica gel (mobile solvent: methylene chloride/isopropanol=15:1)

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

Procedure: 18.16 g (128.7 mmol) of 4-fluoronitrobenzene is added to 100 g (515.0 mmol) of tetraethylene glycol, 73 g (1300 mmol) of finely powdered potassium hydroxide and 500 mg of tetrabutylammonium hydrogen sulfate in 500 ml of toluene at 0° C., and it is stirred overnight at room temperature. 1000 ml of saturated common salt solution is; added, the organic phase is separated and it is dried on magnesium sulfate. It is evaporated to dryness in a vacuum, and the residue is chromatographed in silica gel (mobile solvent: methylene chloride/isopropanol=15:1). added the organic phase is separated it is dried on magnesium sulfate It is evaporated to dryness in a vacuum the residue is chromatographed in silica gel (mobile solvent: methylene chloride/isopropanol=15:1)