3-Nitrophenol → (R)-2,2-dimethyl-4-((3-nitrophenoxy)methyl)-1,3-dioxolane

Participants

Reaction Conditions

Reaction Steps

3-Nitrophenol (130; 2.0 g, 14.37 mmol) was taken up in 20 mL of anhydrous DMF along with anhydrous potassium carbonate (4.96 g, 35.93 mmol) and (R)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane (131; 2.55 mL, 18.68 mmol). The resulting reaction mixture was heated in the microwave reactor, with stirring, at 160° C. for 4 h. The crude reaction mixture was rinsed with water, filtered and extracted with dichloromethane (3×15 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography using ethyl acetate:pentanes to obtain the desired product 132 as an amber-colored oil (52%).

Provenance & Evidence