Sodium hydride → Ethyl 4-[3-(4-{[benzyl(2-methyl-3-nitrophenyl)amino]methyl}phenoxy)phenoxy]butanoate

Participants

Reaction Steps

A solution of the product from Example 61F (0.1000 g, 0.227 mmoles) in DMF (0.57 mL) was treated with NaH (0.0109 g, 0.27 mmoles, 60% dispersion). After 15 min, ethyl 4-bromobutyrate (0.039 mL, 0.27 mmoles) was added and the reaction was stirred overnight. The crude products were diluted with diethyl ether, washed with sat. NH4Cl, extracted with H2O (2×), washed with brine, dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (hexane to 7:1 hexane:ethyl acetate) to provide the title compound as a yellow oil.

Provenance & Evidence