Guaiacol → 1-Pyrrolidinecarboxylic acid, 2-oxo-, 2-methoxyphenyl ester

Participants

Reaction Steps

To a solution of phosgen (6.27 g, 63.3 mmol) in anhydrous benzene (30 ml) was dropwise added under ice-cooling a solution of 2-methoxyphenol (7.86 g, 63.3 mmol) and purified pyridine (5.00 g, 63.3 mmol) in anhydrous benzene (20 ml). The mixture was stirred overnight at room temperature. From a reaction solution were separated white precipitates by filtration, and a filtrate was evaporated under reduced pressure to give a colorless oily material. The oily material was dissolved in anhydrous benzene (20 ml), to which was added a solution of 1-trimethylsilyl-2-pyrrolidinone (9.66 g, 63.3 mmol) in anhydrous benzene (10 ml). The mixture was stirred at room temperature for 30 min. The reaction mixture was evaporated under reduced pressure to dryness to give a solid material. The desired product was separated using column chromatography on silica gel (eluted with benzene-acetone 20:1→1:1).

Provenance & Evidence