2-[tert-butyl(dimethyl)silyl]oxyphenol

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

Procedure: To a stirred solution of catechol (5.5 g; 50 mmol) in 20 mL of dimethylformamide was added imidazole (7.14 g; 105 mmol) and t-butyldimethylsilylchloride (7.53 g; 50 mmol). The reaction mixture was stirred for 3 hours after which time TLC showed the reaction to be complete. The reaction mixture was chromatographed directly onto silica gel and eluted with 5% ethyl acetate in hexane to give 7.4 g (66%) of the monosilyl catechol 16. NMR (CDCl3) δ6.963 (dd, J=8.0, 1.6 Hz, 1H, ArH), 6.891 (dt, J=8.0, 2.0 Hz, 1H, ArH), 6.847 (dd, J=8.0, 1.6 Hz, 1H, ArH), 6.773 (dt, J=7.6, 1.6 Hz, 1H, ArH), 5.518 (s, 1H, OH), 0.996 (s, 9H, CCH3), 0.252 (s, 6H, SiCH3); 13C NMR (CDCl3) δ147.250, 142.550, 122.143, 119.989, 117.835, 114.870, 25.730, 18.193, -4.322. the reaction The reaction mixture was chromatographed directly onto silica gel eluted with 5% ethyl acetate in hexane

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

Procedure: To a stirred solution of catechol (5.5 g; 50 mmol) in 20 mL of dimethylformamide was added imidazole (7.14 g; 105 mmol) and t-butyldimethylsilylchloride (7.53 g; 50 mmol). The reaction mixture was stirred for 3 hours after which time TLC showed the reaction to be complete. The reaction mixture was chromatographed directly onto silica gel and eluted with 5% ethyl acetate in hexane to give 7.4 g (66%) of the monosilyl catechol 16. NMR (CDCl3) δ6.963 (dd, J=8.0, 1.6 Hz, 1H, ArH), 6.891 (dt, J=8.0, 2.0 Hz, 1H, ArH), 6.847 (dd, J=8.0, 1.6 Hz, 1H, ArH), 6.773 (dt, J=7.6, 1.6 Hz, 1H, ArH), 5.518 (s, 1H, OH), 0.996 (s, 9H, CCH3), 0.252 (s, 6H, SiCH3); 13C NMR (CDCl3) δ147.250, 142.550, 122.143, 119.989, 117.835, 114.870, 25.730, 18.193, -4.322. the reaction The reaction mixture was chromatographed directly onto silica gel eluted with 5% ethyl acetate in hexane