HCID 13827091, compound → HCID 504663, compound

Participants

Reaction Conditions

Reaction Steps

Methyl lithium (4.69 ml, 1.4M, Aldrich) was added to a suspension of cuprous iodide (0.62 gm) in anhydrous ether under argon at -78° C. The solution was stirred at -25° C. for 25 min. This solution was added to a solution of 2-ethoxy-5-bromomethyl-4H-3,1-benzoxazin-4-one (200 mg) in 15 ml anhydrous ether and 3 ml dry tetrahydrofuran at -60° C. Reaction was monitored by TLC until reaction completion. The reaction was quenched with saturated ammonium chloride solution and filtered. The filtrate was extracted in the usual manner. The ethereal layer was washed with water, dried over magnesium sulphate and evaporated to give an oil. The material was purified by thick layer chromatography (Rf =0.75, 3-% ethyl acetate: petroleum ether), to give 2-ethoxy-5-ethyl-4H-3,1-benzoxazin-4-one, m.p. 89°-91° C., H NMR: 1.3, 1.5 (2t, 6H, 2CH3), 3.2 (q, 2H, CH2), 4.5 (q, 2H, OCH2CH3), 7.2 (m, 2H, ArH), 7.6 (t, 1H, ArH).

Provenance & Evidence