Dimethylbarbituric acid → Isoindoline

Participants

Reaction Steps

A mixture under N2 of (±)-1-(2-allyloxy-5-chloro-phenyl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (10.35 g, 26.8 mmol, 1.00 eq.), 1,3-dimethylbarbituric acid (8.38 g, 53.6 mmol, 2.00 eq.) and tetrakis(triphenylphosphine) palladium (0) (1.55 g, 1.34 mmol, 0.05 eq.) in MeOH (300 mL) was stirred at r.t. for 5 hours. The mixture was partitioned between AcOEt (250 mL) and water (250 mL). The layers were separated and the aq. phase was extracted with AcOEt (2×100 mL). The comb. org. phases were washed with sat. aq. NaCl soln. (1×250 mL), dried over MgSO4, and concentrated in vacuo. The residue was purified by flash master (column: 340 g, flow: 90 mL/min, Heptane to Heptane+50% AcOEt) to give the desired phenol 30.

Provenance & Evidence