Methyl iodide → Methyl (1-methyl-1,2,3,4-tetrahydro-1-naphthalenyl)(oxo)acetate

Participants

Reaction Conditions

Reaction Steps

Ethyl (2Z)-3,4-dihydro-1(2H)-naphthalenylidene(formylamino)ethanoate (1.31 g, 5.05 mmol, from Reference Example 9) is refluxed with 6N HCL (10 mL) for 1 hour. The mixture is evaporated, dried and the residue taken up in tetrahydrofuran (8 mL) and water (1.7 mL). To this is added 5 N sodium hydroxide solution (3.6 mL, 18.0 mmol) and iodomethane (0.9 mL, 14.5 mmol). While stirring under a nitrogen atmosphere, the reaction mixture is heated in a 70° C. oil bath for 5½ hours. Additional volumes of 5 N sodium hydroxide solution (2.0 mL) and iodomethane (0.3 mL, 4.8 mmol) are added. The reaction mixture is allowed to stir for 2 days at room temperature, then evaporated in vacuo to remove most of the tetrahydrofuran. This is extracted with ethyl acetate and the organic layer then dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give a clear oil, 0.49 g, MS: m/z 233.2 (M+1).

Provenance & Evidence