Water → 2-[4-[2-(tert-Butyldiphenylsilyloxy)ethoxy]phenyl]-3-[4-[2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophene

Participants

Reaction Conditions

Reaction Steps

A mixture of 2.00 g (4.66 mmol) of 2-(4-hydroxyphenyl)-3-[4-[2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophene, 1.86 g (5.12 mmol) of 1-bromo-2-(tert-butyldiphenyl-silyloxy)ethane, and 1.93 g (14.0 mmol) of K2CO3 in 50 mL DMF was heated to 50° C. for 22 h. The reaction was poured into 250 mL of H2O and the mixture extracted with EtOAc (3×100 mL). The combined organic extracts were washed with H2O (2×100 mL), dried over K2CO3, filtered and concentrated in vacuo to give 4.21 g of an oily solid. Purification by flash chromatography (SiO2; 0.1% then 0.2% then 0.5% MeOH in CHCl3 sat'd with NH4OH) afforded 2.76 g (3.88 mmol; 83%) of the title compound as an oil.

Provenance & Evidence