Synthesis
Under nitrogen protection, α-tetralone (25.0 mmol, 3.33 mL), dimethyl carbonate (300 mmol, 25.0 mL), sodium hydride (60% mineral oil dispersion, 50.0 mmol, 2.00 g) and dry methanol (0.1 mL) were mixed. The reaction mixture was heated to 80 °C and stirred continuously for 3 hours. After the reaction was completed, it was cooled to room temperature and the reaction was quenched by slowly adding 3N hydrochloric acid (30.0 mL). The reaction mixture was extracted with ethyl acetate, the organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to give methyl 1,2,3,4-tetrahydro-1-oxo-2-naphthalenecarboxylate (5.06 g, 100% yield) as a reddish brown liquid.
References
[1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 2, p. 292 - 300
[2] Chemistry - A European Journal, 2017, vol. 23, # 54, p. 13309 - 13313
[3] Tetrahedron, 1995, vol. 51, # 12, p. 3587 - 3606
[4] Synthesis, 2003, # 15, p. 2292 - 2294
[5] Journal of Organic Chemistry, 2007, vol. 72, # 10, p. 3702 - 3712
