Methane → HCID 13537721, compound

Participants

Reaction Steps

Using the procedure described by Baker et al., Journ. of Chem. Soc. Perkin Trans. 1, 3, 677-685 (1979), ethyl cyanoacetate (3.5 g, 0.031 mol) was added to NaOMe solution (prepared from 0.72 g of sodium metal in 50 ml of MeOH), followed by 1 (5.77 g, 0.031 mol). The mixture was refluxed for 15 minutes, cooled and divided into two equal parts. The first portion was acidified with 2N HCl to pH 2-3 and extracted with CH2Cl2. The extracts were washed, dried over MgSO4, and evaporated to give an orange-colored solid. After decolorizing with Nuchar activated carbon in ethyl acetate and recrystallizing from EtOAc-hexane, white, fluffy crystals, of 3-(methoxycarbonyl)-5-(ethoxycarbonyl)-6-methyl-2-pyrone were obtained: 0.22 g, 6% yield; mp=94°-96° C.; NMR (DMSO-d6) δ 1.2-1.5 (t, 3H), 2.7 (s, 3H), 3.8 (s, 3H), 4.1-4.6 (q, 2H), 8.5 (s, 1H); IR (KBr) 1700-1730 cm-1 (C=O of Me and Et ester), 1770 cm-1 (C=O of pyrone).

Provenance & Evidence