Phthalimide → HCID 20601400, compound

Participants

Reaction Steps

To a stirred mixture of 1.4 g (5.8 mmol.) 4′-hydroxymethyl-biphenyl-3-carboxylic acid methyl ester, 1.0 g (6.9 mmol.) phthalimide, and 1.8 g (6.9 mmol.) triphenylphosphine in 25 mL tetrahydrofuran at 0° C. was added 1.2 ml (7.5 mmol.) diethylazodicarboxylate. The mixture was warmed to ambient temperature and stirred for 18 hours. The mixture was poured into water and extracted with ethyl acetate. The ethyl acetate extracts were combined then washed successively with 1N NaOH, 1N HCl, water, brine then dried (MgSO4) and concentrated in vacuo to give a solid. Trituration with diethyl ether gave 3.0 g 4′-[1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl]-biphenyl-3-carboxylic acid methyl ester as a solid.

Provenance & Evidence