Sodium Methoxide → HCID 14217110, compound

Participants

Reaction Steps

A solution consisting of 19 g (0.165 mol) of oxazolones 3 and 100 ml of methanol was treated with solid sodium methoxide until the reaction mixture was slightly basic (pH 9 as indicated by moist pH paper). The solution was stirred for 3/4 hr. at room temperature. The reaction mixture was concentrated in vacuo, and the residue taken up in 500 ml of ether. Petroleum ether (bp 35°-60°) was added until the solution was slightly turbid. An additional portion of ether was added to clear the turbidity and the resultant solution was treated with charcoal and filtered through Celite®. The solvents were removed in vacuo, and the residue dried at 0.1 mm. Crystallization from ether/petroleum ether (bp 35°-60°) yielded Z-2-acetamido-4-methoxy-2-butenoic acid methyl ester (4): mp 60°-61°; IR (CHCl3) 3415, 1720, 1700, 1500 cm-1 ; UV (EtOH) λmax 226 nm (ε7500); NMR (CDCl3) δ 7.5 (broad, 1H, NH), 6.7 (t, 1H, --CH2CH=), 4.1 (d, 2H, --CH2CH=), 3.8 (s, 3H, CH3O2C--), 3.4 (s, 3H, CH3OCH2 --), 2.14 (s, 3H, CH3CONH--). (Calcd. for C8H13NO4 : C, 51.33; H, 7.00; N, 7.48. Found: C, 51.20; H, 7.13; N, 7.69.)

Provenance & Evidence