Acetic Anhydride → Methyl 5-acetyl-3-methylfuran-2-carboxylate

Participants

Reaction Steps

Tin (IV) chloride (2.5 ml) is added to a solution of 3-methyl-furan-2-carboxylic acid methyl ester (1.0 g) and acetic anhydride (3.2 ml) in dichloromethane (8 ml) at 0° C. After 1 hour 30 minutes at 0° C. the reaction mixture is poured into a cold 10% Na2CO3 aqueous solution. The reaction mixture is filtered through a plug of Celite and the filtration cake is washed with dichloromethane. The aqueous phase is extracted two times with dichloromethane. The combined organic phases are washed once with water and with a saturated aqueous solution of NaCl, dried over MgSO4 and concentrated in vacuo. The crude product is purified on a semi-preparative HPLC to yield 5-Acetyl-3-methyl-furan-2-carboxylic acid methyl ester (0.5 g) as a white solid. MS (HPLC/MS): 183 (MH+). Retention time: 1.09 min.

Provenance & Evidence