Lithium Hydroxide → HCID 69830566, compound

Participants

Reaction Steps

To a solution of 2-diazo-1-[3-(2,2-dimethyl-[1,3]-dioxolan-4-ylmethoxy)-2-nitrophenyl]ethanone (0.9 g, 2.8 mmol) in 30 mL of methanol at room temperature was added dropwise a solution of silver benzoate (84 mg, 13%) in 4.2 mL of triethylamine. The solution turned greenish and then brown, black precipitate formed. After stirring for 1.5 h, it was filtered through celite and the filtrate was concentrated. The residue was then purified on a silica gel column with 20% ethyl acetate in hexane to afford 0.75 g of [3-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-2-nitrophenyl] acetic acid methyl ester. The above ester (0.52 g, 1.6 mmol) was then hydrolyzed by stirring with lithium hydroxide (0.27 g) in 5 mL of methanol at room temperature to give 0.5 g of [3-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-2-nitrophenyl] acetic acid.

Provenance & Evidence