Methanol → HCID 22613105, compound

Participants

Reaction Steps

To a 200 mL round bottomed flask with a stirring bar and a nitrogen inlet was added ethyl 4-(benzyl-3-methoxy-2-methoxyethoxyphenyl)-2,4-dioxobutyrate (1.48 g, 3.57 mmol), THF (30 mL), methanol (30 mL), and sodium hydroxide solution (18 mL of a 1 N solution in water, 18 mmol). This mixture was stirred 2 h at ambient temperature. The organic solvents were removed in vacuo and the aqueous residue was diluted with 30 mL of water. This solution was washed with ethyl ether (2×50 mL) then acidified with 1N HCl. This mixture was extracted with ethyl ether (100 mL). The ether solution was washed with water and brine. Drying (MgSO4), filtration and removal of the solvent in vacuo gave a yellow oil. This material was crystallized by dissolving in 1:1 ether-hexane (−5mL) and storing in a freezer over night. The crystalline product was collected by filtration on a frit and dried in vacuo at ambient temperature to give 4-(benzyl-3-methoxy-2-methoxyethoxyphenyl)-2,4-dioxobutyric acid as yellow needles. MP: 83-85° C. Anal. Calc'd for C21H22O7: C, 65.28; H, 5.74; Found: C, 65.28; H, 6.05. 1H NMR (CDCl3): δ3.39 (s, 3H); 3.71 (t, j=4 Hz, 2H); 3.82 (s, 3H); 3.96 (s, 2H); 4.21 (t, j=4 Hz, 2H); 6.90 (d, j=2Hz, 1H); 7.28 (m, 6H); 9.60 (br s, 1H).

Provenance & Evidence