Hydrochloric Acid → Methyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

A suspension of 60% dispersion of sodium hydride in mineral oil (1.64 g, 41 mmol) in dimethyl carbonate (50 mL) was treated dropwise with alpha-tetralone (4.6 mL, 34 mmol). The mixture was heated at 90° C. for 20 minutes, cooled to ambient temperature, treated with 2 M HCl (40 mL), and extracted with EtOAc (100 mL and 25 mL). The combined EtOAc layers were washed with brine, dried (MgSO4), filtered, concentrated under reduced pressure and chromatographed on silica gel eluting with a gradient of hexane:EtOAc (20:1 and 10:1) to provide the title compound. MS (M+H)+ m/z 205.

Provenance & Evidence