[2-[[tert-butyl(dimethyl)silyl]oxymethyl]phenyl]methanol

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

Procedure: To a solution of 1,2-benzenedimethanol (2 g) and imidazole (1.13 g) in N,N-dimethylformamide (30 mL) was added tert -butyldimethylchlorosilane (2.08 g), and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with ethyl acetate, and the resulting mixture was washed with 1 mol/L hydrochloric acid, water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=3/2) to give the title compound (1.46 g). the resulting mixture was washed with 1 mol/L hydrochloric acid, water and brine successively dried over anhydrous magnesium sulfate The solvent was removed under reduced pressure the residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=3/2)

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

Procedure: To a solution of 14.074 g (101.86 mM) of 1,2-benzenedimethanol in 100 ml of 1,2-dimethoxyethane was added 4.07 g (102 mM) of a liquid paraffin suspension of 60% sodium hydride at room temperature and the mixture was stirred at the prevailing temperature for one hour. To this reaction mixture was added a solution of 15.4 g (102 mM) of tert-butylchlorodimethylsilane in 50 ml of 1,2-dimethoxyethane dropwise, and the mixture was stirred at room temperature overnight. This reaction mixture was poured in water and extracted with 3 portions of ethyl acetate. The organic layers were combined and dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1 to 3/1) to provide the title compound. the mixture was stirred at room temperature overnight extracted with 3 portions of ethyl acetate dried over MgSO4 the solvent was distilled off under reduced pressure The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1 to 3/1)

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

Procedure: To a solution of 1,2-benzenedimethanol (500 mg, 3.62 mmol), N,N-diisopropylethylamine (0.76 mL, 4.4 mmol) in 3.6 mL of dichloromethane was added tert-butyldimethylsilyl chloride (573 mg, 3.80 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred for 1 day. The reaction mixture was diluted with diethyl ether, and the solution was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 85/15) to obtain 2-[(tert-butyldimethylsilyloxy)methyl]benzylalcohol as a colorless oil (520 mg, 57%). the solution was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine dried over MgSO4 After filtration the filtrate was concentrated in vacuo the residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 85/15)

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

Procedure: To a solution of 1,2-benzenedimethanol (2 g) and imidazole (1.13 g) in N,N-dimethylformamide (30 mL) was added tert -butyldimethylchlorosilane (2.08 g), and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with ethyl acetate, and the resulting mixture was washed with 1 mol/L hydrochloric acid, water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=3/2) to give the title compound (1.46 g). the resulting mixture was washed with 1 mol/L hydrochloric acid, water and brine successively dried over anhydrous magnesium sulfate The solvent was removed under reduced pressure the residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=3/2)