1,8-Diazabicyclo(5.4.0)undec-7-ene → Phenylmethyl 3-(2,4-dichlorophenyl)pyrrole-2-carboxylate

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Reaction Steps

DBU (1 eq) was added to a stirred solution of 2,4-Dichloronitrostyrene (1) (1 eq) and benzyl 2-isocyanoacetate (0.9 eq) in THF at −78° C. under N2. The reaction was allowed to warm to room temperature over 2 h. The reaction could be followed by TLC eluting with CHCl3 (Rf0.3). After stirring for an additional 12 h, the reaction was diluted with CH2Cl2 and EtOAc. The organic mixture washed with 0.1 N HCl, water, sat. aq. NaHCO3, brine, dried (Na2SO4), filtered and concentrated under reduced pressure to an oil. The crude product was purified using silica column chromatography eluting with CHCl3 to obtain pure phenylmethyl 3-(2,4-dichlorophenyl)pyrrole-2-carboxylate (2) (15% yield).

Provenance & Evidence