Pyridine → HCID 22713764, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.0 g (7 mmol) of 3-oxocyclopentyl acetic acid in dichloromethane (18 mL) and DMP (1 mL), was added 0.68 mL (7.7 mmol) oxalyl chloride. After 30 min, the solvent was removed in vacuo. The residue was dissolved in dichloromethane (20 mL), cooled to 0-5° C., and 1.29 g of 3,4,5-trimethoxyaniline (0.63 mmol) was added followed by 0.68 mL of pyridine (8.4 mmol). After 15 min, the reaction was allowed to warm to ambient temperature. After 2 h, the reaction was rinsed with 1N HCl, followed by aq. sodium bicarbonate, and water (3×). The organic layer was dried, the solvent removed in vacuo and the residue chromatographed on a silica gel with 2% methanol in methylene chloride to yield 0.25 g of the title compound. MS(ES+)m/z=308.

Provenance & Evidence