Acetic Acid → Ethyl (2Z)-3,4-dihydro-1(2H)-naphthalenylidene(formylamino)ethanoate

Participants

Reaction Steps

To a stirred slurry of potassium t-butoxide (4.7 g, 42.0 mmol) in 30 mL tetrahydrofuran at 0° C. is added ethyl isocyanoacetate (4.53 g, 40.0 mmol). This is stirred for 30 mins whereupon a solution of β-tetralone (5.88 g, 40.0 mmol) in tetrahydrofuran (20 mL) is added dropwise. The reaction mixture is allowed to warm to room temperature and stirred for 3 hours. The reaction mixture is then recooled in an ice bath and to this is added acetic acid (2.5 g, 41.6 mmol), allowed to warm to room temperature and stirred for an additional 30 mins. The solvent is removed in-vacuo and the residue partitioned between water and ethyl acetate. The organic layer is washed with water and brine, dried over sodium sulfate, filtered, evaporated and crystallized from cyclohexane to give 4.67 g of a white solid (contains some E-isomer), MS: m/z 260.2 (M+1).

Provenance & Evidence