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56 °C, 24 h) in glacial acetic acid (2.7 mL) was cooled with an ice/water bath for 20 min at which time concentrated HN03 (2.7 mL, 0 °C) was added dropwise to the pasty solid over the course of 3 min with rapid stirring. Water (10 mL, 5 °C) was added after 30 min followed by a 45-min dropwise addition of 10% NaHC03 (65 mL). The mixture was extracted with dichloromethane (4 X 15 mL), and the combined extracts were washed with brine. Drying and evaporation provided 36 as an orange solid: 23.2 mg (83% yield, pure by RPHPLC, solvent A, iR 6.8 min); mp [226][227][228] °C (lit. mp [224][225][226][227] °C,5 222-224 °C9); Rf (Si02, ethyl acetate) 0.60; NMR (250 MHz) 2.01 (s, 3 H, CH3), 2.68 (tt, 2 H, NCH2CH2), 3.14 (t, 2 H, NCH2CH2CH2, =7=7 Hz), 4.06 (s, 3 H,

5 2-Hydroxymethyl-5-methoxy-4-H-pyran-4-one (1) reacts with aniline and six aniline derivatives in very dilute aqueous hydrochloric acid at reflux temperature to give the N-aryl-y-pyridone. A second procedure utilizes the aromatic amine hydrochloride by reacting it with 1 in aqueous medium at reflux temperature. p-Nitroaniline hydrochloride and 1 give the N-aryl-y-pyridone in 65% yield, as opposed to 12% from the dilute acid procedure.

α‐Hydroxymaltol (Ia) liefert in üblicher Weise die Ether (Ib)‐(Id).