Nitromethane → 6-(Nitromethyl)spiro[2.5]octan-6-ol

Participants

Reaction Steps

To 4M solution of sodium methoxide (14 mL) in methanol (10 mL) was added a solution of spiro[2.5]octan-6-one (4.6 g, 0.031 mol) and nitromethane (2.3 mL, 0.042 mol) in methanol (20 mL) at room temperature and stirred overnight. The reaction was quenched with acetic acid (4.5 mL) and water (50 mL) and the volatiles were removed under reduced pressure. The residue was extracted with dichloromethane (2×50 mL), and the combined extracts were dried, filtered and evaporated. The residue was purified by flash chromatography to afford the desired product (3.2 g, 52%).

Provenance & Evidence