[2-(2-{2-[2-(2-Bromo-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxymethyl]benzene

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

Procedure: To an ice-cooled mixed suspension of sodium hydride (350 mg, 8.8 mmol; 60% in mineral oil) in THF (4.5 ml) and DMF (1.5 ml), a mixed solution of Compound 45 (1.0 g, 1.7 mmol) in THF (4.5 ml) and DMF (1.5 ml) was gradually added, and this was followed by stirring for 30 minutes. A solution of Compound 20 (2.7 g, 6.8 mmol) in THF (4 ml) was added thereto, and this was followed by stirring for 20 minutes. After the ice bath was removed, stirring was further conducted at room temperature for 4 hours. After the product was again immersed in the ice bath, water was carefully added to stop the reaction, and this was followed by concentration under reduced pressure. Extraction from ethyl acetate was conducted, and the combined organic phases were washed with saturated brine and dried with anhydrous sodium sulfate. Filtration and concentration under reduced pressure were conducted, after which the residue obtained was purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (ethyl acetate-ethyl acetate:methanol 19:1)) to yield Compound 46 (light-yellow oil 1.22 g, 59%). mixed by stirring for 20 minutes After the ice bath was removed stirring was further conducted at room temperature for 4 hours was carefully added the reaction this was followed by concentration under reduced pressure Extraction from ethyl acetate the combined organic phases were washed with saturated brine dried with anhydrous sodium sulfate Filtration and concentration under reduced pressure after which the residue obtained was purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (ethyl acetate-ethyl acetate:methanol 19:1))

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

Procedure: To an ice-cooled suspension of sodium hydride (800 mg, 20 mmol; 60% in mineral oil) in THF (15 ml), a solution of Compound 22 (1.2 g, 2.1 mmol) in THF (20 ml) was gradually added; this was followed by stirring for 20 minutes. A solution of Compound 20 (1.7 g, 4.3 mmol) in THF (12 ml) was added thereto, and this was followed by stirring for 20 minutes. After the ice bath was removed, stirring was further conducted at room temperature for 2 hours. Water was carefully added to stop the reaction, and this was followed by concentration under reduced pressure. Extraction from methylene chloride was conducted, and the combined organic phases were washed with saturated brine and dried with anhydrous sodium sulfate. After filtration and concentration under reduced pressure, the residue obtained was purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (n-hexane:ethyl acetate 2:1-1:1)) to yield Compound 23 (light-yellow oil 1.56 g, 84%). by stirring for 20 minutes After the ice bath was removed stirring was further conducted at room temperature for 2 hours Water was carefully added the reaction this was followed by concentration under reduced pressure Extraction from methylene chloride the combined organic phases were washed with saturated brine dried with anhydrous sodium sulfate After filtration and concentration under reduced pressure the residue obtained was purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (n-hexane:ethyl acetate 2:1-1:1))

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

Procedure: To a solution of Compound 19 (2.04 g, 6.21 mmol) in methylene chloride (20 ml), a solution of carbon tetrabromide (4.12 g, 12.4 mmol) in methylene chloride (10 ml) was added at room temperature; after cooling with ice, triphenylphosphine (2.51 g, 12.4 mmol) was added. The water bath was removed, and this was followed by stirring at room temperature for 1 hour. After concentration under reduced pressure, the residue obtained was purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (n-hexane:ethyl acetate 2:1-1:1)) to yield Compound 20 (light-yellow oil 2.14 g, 88%). was added The water bath was removed After concentration under reduced pressure the residue obtained was purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (n-hexane:ethyl acetate 2:1-1:1))