tert-butyl-[4-(chloromethyl)phenoxy]-dimethylsilane

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: The procedure of Preparation Example 7 was repeated, except that 2.058 g of 4-(tert-butyldimethylsilyloxy)benzyl chloride was used in place of 4-benzyloxybenzyl chloride, and 0.946 g of 4-aminobenzonitrile was used in place of 4-aminophenol. The resulting crude product was purified by silica gel column chromatography (using a 3:1 mixture of hexane and ethyl acetate as the eluent) to obtain 0.682 g of 4-[N-(4-tert-butyldimethylsilyloxybenzyl)amino]benzonitrile. The procedure of Preparation Example 7 The resulting crude product was purified by silica gel column chromatography ( a 3:1 mixture of hexane and ethyl acetate as the eluent)

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

Procedure: 224 mg of 4-[N(4-methoxyphenyl)amino]benzonitrile was dissolved in 1.2 ml of N,N-dimethylformamide, and 48 mg of sodium borohydride was added thereto under cooling with ice, followed by stirring at room temperature for 30 minutes. The previously prepared 4-(t-butyldimethylsilyloxy)benzyl chloride was dissolved in 1.2 ml of N,N- dimethylformamide and added to the reaction mixture under cooling with ice, followed by stirring at room temperature for 2 days. After water was added to the reaction mixture, the product was extracted with ethyl acetate. After the extract was washed with water and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was dissolved in 1.2 ml of tetrahydrofuran, and 1.2 ml of a 1 M tetrahydrofuran solution of tetrabutylammonium fluoride was added thereto, followed by stirring at room temperature for 15 minutes. After a saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, the product was extracted with ethyl acetate. After the extract was washed with water and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (using ethyl acetate as the eluent) to obtain 229 mg of 4-[N-(4-hydroxybenzyl)-N-(4-methoxyphenyl)amino]benzonitrile. under cooling with ice added to the reaction mixture under cooling with ice by stirring at room temperature for 2 days the product was extracted with ethyl acetate After the extract was washed with water dried over anhydrous sodium sulfate the solvent was distilled off under reduced pressure The resulting residue was dissolved in 1.2 ml of tetrahydrofuran 1.2 ml of a 1 M tetrahydrofuran solution of tetrabutylammonium fluoride was added by stirring at room temperature for 15 minutes After a saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture the product was extracted with ethyl acetate After the extract was washed with water dried over anhydrous sodium sulfate the solvent was distilled off under reduced pressure The resulting crude product was purified by silica gel column chromatography (

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

Procedure: A mixture composed of 286 mg of 4-(tert-butyldimethylsilyloxy)benzyl alcohol and 1.75 ml of thionyl chloride was heated under reflux for 1 hour. After the thionyl chloride was distilled off from the reaction mixture under reduced pressure, its azeotropic distillation with toluene was carried out three times to remove any thionyl chloride. Thus, there was obtained 4-(tert-butyldimethylsilyloxy)benzyl chloride. was heated under reflux for 1 hour After the thionyl chloride was distilled off from the reaction mixture under reduced pressure, its azeotropic distillation with toluene to remove any thionyl chloride