Ethyl Acetate → 8-methoxycarbonyl 4H-pyrrolo[2,1-c][1,4]-benzoxazine

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Reaction Steps

Diethyl azodicarboxylate (2.3 ml) was added dropwise to the mixture of methyl 4-hydroxy-3-(2-hydroxymethylpyrrol-1-yl)benzoate (2.5 g) and triphenylphosphine (4.0 g) in tetrahydrofuran (50 ml) under ice-cooling and the mixture was stirred for 2 hours at ambient temperature. The mixture was poured into the mixture of ethyl acetate and water. The separated organic layer was washed with brine and dried over magnesium sulfate. Evaporation of the solvent gave the residue, which was purified by column chromatography on silica gel eluting with chloroform. The eluted fractions containing the desired product were collected and evaporated in vacuo to give 8-methoxycarbonyl 4H-pyrrolo[2,1-c][1,4]-benzoxazine (0.61 g).

Provenance & Evidence