4-(((Tert-Butyldimethylsilyl)Oxy)Methyl)Phenol

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

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

Procedure: A mixture of 1.24 g (0.01 mole) of 4-hydroxymethylphenol, 1.8 g (0.012 mole) of tert-butyldimethylsilyl chloride, 1.7 g (0.025 mole) of imidazole and 3 ml of dimethylformamide was stirred under nitrogen at room temperature for 12 h. The reaction mixture was poured into water and extracted with three portions of ether. Ether extracts were combined and washed successively with water and saturated NaCl solution and then dried (Na2SO4). The ether solution was concentrated in-vacuo and the resultant crude product was purified by flash chromatography (silica; 10% ethyl acetate in hexanes) to give the title compound as a colorless oil. extracted with three portions of ether washed successively with water and saturated NaCl solution dried (Na2SO4) The ether solution was concentrated in-vacuo the resultant crude product was purified by flash chromatography (silica; 10% ethyl acetate in hexanes)

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

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

Procedure: Tetrabutylammonium fluoride (1 M THF, 44 mL, 44 mmol) was added to a 0° C. solution of 1-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)benzene (14 g, 40 mmol) in THF (400 mL). The reaction was stirred for 30 minutes, then poured into a mixture of saturated NH4Cl and Et2O. The layers were separated and the aqueous phase was extracted twice with Et2O. The organics were combined, washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was chromatographed (1:9 EtOAc/hexanes) to provide the product as a colorless oil (8.0 g, 85%). The layers were separated the aqueous phase was extracted twice with Et2O washed with brine dried over MgSO4 concentrated under reduced pressure The residue was chromatographed (1:9 EtOAc/hexanes)

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

Procedure: A mixture of 1.24 g (0.01 mole) of 4-hydroxymethylphenol, 1.8 g (0.012 mole) of tert-butyldimethylsilyl chloride, 1.7 g (0.025 mole) of imidazole and 3 ml of dimethylformamide was stirred under nitrogen at room temperature for 12 h. The reaction mixture was poured into water and extracted with three portions of ether. Ether extracts were combined and washed successively with water and saturated NaCl solution and then dried (Na2SO4). The ether solution was concentrated in-vacuo and the resultant crude product was purified by flash chromatography (silica; 10% ethyl acetate in hexanes) to give the title compound as a colorless oil. extracted with three portions of ether washed successively with water and saturated NaCl solution dried (Na2SO4) The ether solution was concentrated in-vacuo the resultant crude product was purified by flash chromatography (silica; 10% ethyl acetate in hexanes)