1-Iodopropane → 2-(4-Chloro-2-[1,3]dioxolan-2-yl-phenoxy)-2-propyl pentanoic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

Lithium bis(trimethylsilyl)amide (26 mL, 26 mmol, 1 M in THF) was slowly added to a solution of 2-(4-Chloro-2-[1,3]dioxolan-2-yl-phenoxy)-pentanoic acid ethyl ester (6.6 g, 20 mmol) in anhydrous THF (60 mL) at −78° C. After the mixture was stirred for 30 min at −78° C., 1-iodopropane (4 mL, 40 mmol) was added. The mixture was allowed to warm to room temperature and stirred for 2 h. Then the mixture was diluted with ethyl acetate, washed with a saturated aqueous solution of NH4Cl, and the organic layer was separated, dried over anhydrous Na2SO4 and concentrated to give the title compound as a yellow oil (5 g).

Provenance & Evidence