Pyridine → 2-Acetyl-5-methoxy-3-oxo-pentanoic acid methyl ester

Participants

Reaction Steps

Pyridine (5.3 ml, 65.92 mmol) was dropped within 3 min to an ice cooled solution of 5-methoxy-3-oxo-pentanoic acid methyl ester (5.28 g, 32.96 mmol) and anhydrous magnesium chloride (3.14 g, 32.96 mmol) in dichloromethane (50 ml). Acetic anhydride (3.27 ml, 34.6 mmol) was added within 3 min. The reaction mixture was stirred over night at RT and after partial removal of the solvent under reduced pressure it was partitioned between ether and 1 N HCl/water. The ether solution was concentrated under reduced pressure to give 5.87 g (29 mmol, 88%) 2-acetyl-5-methoxy-3-oxo-pentanoic acid methyl ester.

Provenance & Evidence