METHYL 1-OXO-1,2,3,4-TETRAHYDRONAPHTHALENE-2-CARBOXYLATE

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. cooled to ambient temperature extracted with EtOAc (100 mL and 25 mL) The combined EtOAc layers were washed with brine dried (MgSO4) filtered concentrated under reduced pressure chromatographed on silica gel eluting with a gradient of hexane:EtOAc (20:1 and 10:1)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. cooled to ambient temperature extracted with EtOAc (100 mL and 25 mL) The combined EtOAc layers were washed with brine dried (MgSO4) filtered concentrated under reduced pressure chromatographed on silica gel eluting with a gradient of hexane:EtOAc (20:1 and 10:1)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under an argon atmosphere, a mixture of sodium hydride (60% dispersion in mineral oil, 887 mg, 22.0 mmol), dimethyl carbonate (15 mL) and 3,4-dihydronaphthalen-1(2H)-one (1.46 g, 10.0 mmol) was stirred at 80° C. for 3.5 hr. The reaction mixture was quenched with diluted hydrochloric acid, and extracted with ethyl acetate. The organic layer was dried over sodium carbonate, filtrated, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/0→5/1) to give the title compound as a white solid. The reaction mixture was quenched with diluted hydrochloric acid extracted with ethyl acetate The organic layer was dried over sodium carbonate filtrated concentrated under reduced pressure The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/0→5/1)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under an argon atmosphere, a mixture of sodium hydride (60% dispersion in mineral oil, 887 mg, 22.0 mmol), dimethyl carbonate (15 mL) and 3,4-dihydronaphthalen-1(2H)-one (1.46 g, 10.0 mmol) was stirred at 80° C. for 3.5 hr. The reaction mixture was quenched with diluted hydrochloric acid, and extracted with ethyl acetate. The organic layer was dried over sodium carbonate, filtrated, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/0-5/1) to give the title compound as a white solid. The reaction mixture was quenched with diluted hydrochloric acid extracted with ethyl acetate The organic layer was dried over sodium carbonate filtrated concentrated under reduced pressure The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/0-5/1)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. cooled to ambient temperature extracted with EtOAc (100 mL and 25 mL) The combined EtOAc layers were washed with brine dried (MgSO4) filtered concentrated under reduced pressure chromatographed on silica gel eluting with a gradient of hexane:EtOAc (20:1 and 10:1)