Methyl acetoacetate → HCID 57559686, compound

Participants

Reaction Steps

To a dispersion of sodium hydride (95%) (1.00 g, 41.7 mmol, 2.1 equiv) in anhydrous benzene (250 ml) under nitrogen was added dropwise methyl acetoacetate (6.5 ml, 7.00 g, 60.3 mmol, 3.1 equiv) and the mixture was stirred at room temp for 1 hour. 2-ethoxy-4H-naphtho[2,3-d][1,3]oxazin-4-one (1-2) (4.72 g, 19.5 mmol, 1.0 equiv) was added and the reaction continued stirring at room temperature for 20 hours. The reaction was quenched with water and the organic layer was separated, and extracted three times with water. The emulsion and combined aqueous layers were made acidic with conc. HCl and stirred for 20 hours. The solid precipitate was filtered and dried to yield methyl (2Z)-2-acetyl-3-{3-[(ethoxycarbonyl)amino]-2-naphthyl}-3-hydroxyprop-2-enoate (1-3) as a yellow solid. LRMS m/z (M+H) 358.3 found, 358.1 required.

Provenance & Evidence