Diethyl methylmalonate → (+/-)-2-(2-(2-Naphthyl)benzyl)propionic acid

Participants

Reaction Conditions

Reaction Steps

70 g (0.37 mmol) of diethyl methylmalonate dissolved in 50 cm3 of H2O-free EtOH were added dropwise at room temperature to 8.5 g (0.37 mmol) of sodium in 100 cm3 of H2O-free EtOH. Subsequently, 110 g (0.37 mmol) of 14 in 200 cm3 of H2O-free EtOH were added dropwise and the mixture was heated under reflux for 3 hours. 62 g (1.1 mol) of KOH dissolved in 100 cm3 of H2O were added at room temperature and the mixture was heated under reflux for a further 4 hours. The solvents were removed under reduced pressure, the residue was admixed with H2O until completely dissolved and acidified with concentrated aqueous HCl to a pH of 1. The precipitate formed was filtered off with suction, dried and heated at 130° C. for 1 hour. This gave 90 g (84%) of 15 as a viscous oil.

Provenance & Evidence