[4-[2-[tert-butyl(dimethyl)silyl]oxyethoxy]phenyl]methanol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: At 0° C., iodine (1.2 eq.) and imidazole (1.2 eq.) were added to a CH2Cl2 solution (0.05 M) of triphenylphosphine (1.2 eq.). The resulting yellow-orange suspension was stirred at 0° C. for 10 min and then at RT for 15 min. Finally, [4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethoxy)phenyl]methanol from the previous step (1 eq.) was added over 30 min as a 0.2 M CH2Cl2 solution. After another 10 h of stirring at RT, the volatiles were removed in vacuo. The resulting brown residue was suspended in ether and rapidly passed through a plug of SiO2. Removal of the volatiles in vacuo afforded the title compound as a pink oil. at RT for 15 min After another 10 h of stirring at RT the volatiles were removed in vacuo Removal of the volatiles in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: At 0° C., iodine (1.2 eq.) and imidazole (1.2 eq.) were added to a CH2Cl2 solution (0.05 M) of triphenylphosphine (1.2 eq.). The resulting yellow-orange suspension was stirred at 0° C. for 10 min and then at RT for 15 min. Finally, [4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethoxy)phenyl]methanol from the previous step (1 eq.) was added over 30 min as a 0.2 M CH2Cl2 solution. After another 10 h of stirring at RT, the volatiles were removed in vacuo. The resulting brown residue was suspended in ether and rapidly passed through a plug of SiO2. Removal of the volatiles in vacuo afforded the title compound as a pink oil. at RT for 15 min After another 10 h of stirring at RT the volatiles were removed in vacuo Removal of the volatiles in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: At 0° C., iodine (1.2 eq.) and imidazole (1.2 eq.) were added to a CH2Cl2 solution (0.05 M) of triphenylphosphine (1.2 eq.). The resulting yellow-orange suspension was stirred at 0° C. for 10 min and then at RT for 15 min. Finally, [4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethoxy)phenyl]methanol from the previous step (1 eq.) was added over 30 min as a 0.2 M CH2Cl2 solution. After another 10 h of stirring at RT, the volatiles were removed in vacuo. The resulting brown residue was suspended in ether and rapidly passed through a plug of SiO2. Removal of the volatiles in vacuo afforded the title compound as a pink oil. at RT for 15 min After another 10 h of stirring at RT the volatiles were removed in vacuo Removal of the volatiles in vacuo