Methanol → Methyl 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate

Participants

Reaction Steps

To a solution of 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid (10.0 g, 52.6 mmol) in THF (52.6 mL) and MeOH (10.64 mL, 263 mmol) at rt was added trimethylsilyldiazomethane (2.0 M in diethyl ether, 79 mL, 158 mmol) dropwise until the solution turned yellow and gas evolution ceased. The reaction was then concentrated under reduced pressure to give methyl 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate (10.72 g, 52.5 mmol, 100% yield) as a brown solid. MS ESI calcd for C12H12O3 [M+H]+ 205, found 205. 1H NMR (500 MHz, DMSO) δ 7.94 (d, J=8.1 Hz, 1H), 7.91 (s, 1H), 7.85 (dd, J=8.1, 1.6 Hz, 1H), 3.86 (s, 3H), 2.99 (t, J=6.0 Hz, 2H), 2.66-2.61 (m, 2H), 2.09-2.00 (m, 2H).

Provenance & Evidence