Ethane, 2-bromo-1,1-diethoxy- → 2-Phthalimidoacetaldehyde Diethyl Acetal

Participants

Reaction Conditions

Reaction Steps

A three-necked round-bottomed flask fitted with an efficient stirrer and a reflux condenser was charged with potassium phthalimide (150 g, 0.81 mol) and 2-bromo-1,1-diethoxy-ethane (196 g, 1.0 mol) and DMF (500 mL). The stirrer was started and the mixture was heated for about 3-4 h in an oil bath maintained at 150° C. The solvent DMF was removed under reduced pressure. The residue was purified by column chromatography to afford pure 2-(2,2-diethoxyethyl)isoindoline-1,3-dione (185 g, yield 87%). 1H NMR (400 MHz, MeOD): 1.16 (t, 6H), 3.48-3.60 (m, 2H), 3.68-3.75 (m, 2H), 3.76-3.89 (d, 2H), 4.89 (t, 1H), 7.68-7.75 (m, 2H), 7.85-7.96 (m, 2H). MS (E/Z): 264 (M+H+).

Provenance & Evidence