Methanol → HCID 68774376, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,2-dimethyl-1,3-dioxane-4,6-dione (5.0 g, 34.6 mmol) and MeOH (1.4 mL, 34.6 mmol) was heated at 80° C. for 18 h. The reaction was concentrated, the residue (2.05 g, 17.3 mmol) was dissolved in CH3CN (10 mL) and added to a solution of HOBt (2.3 g, 17.3 mmol), EDCI.HCl (3.3 g, 17.3 mmol), N,N-diisopropylethylamine (3.01 mL, 17.3 mmol) and N′-hydroxybenzimidamide (2.0 g, 8.5 mmol) in CH3CN (5 mL). The reaction was stirred at 40° C. for 18 h under N2, and upon completion, diluted with EtOAc and washed with H2O (2×). The combined organic layers were dried over Na2SO4, concentrated and purified by flash-chromatography (0-50% EtOAc in Hexane). The resulting residue was dissolved in CH3CN (10 mL), and heated in a microwave reactor (110° C., 30 min). Upon completion, the solvent was removed in vacuo and the residue was purified by flash-chromatography (0-50% EtOAc in Hexane) to yield methyl 2-(3-phenyl-1,2,4-oxadiazol-5-yl)acetate as a yellow oil (700 mg, 38%). 1H NMR (500 MHz, DMSO-d6): δ 3.72 (s, 3H), 4.41 (s, 2H), 7.56-7.62 (m, 3H), 8.01-8.04 (m, 2H). MS(M+H, 219).

Provenance & Evidence