1-methyl-3,4-dihydro-1H-naphthalen-2-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Propargylamine (0.21 mL) is added to a microwave oven suited vessel charged with a stir bar, 1-methyl-2-tetralone (0.50 mL), NaAuCl4*2H2O (27 mg), and ethanol (3 mL) (caution: a very exothermic reaction may evolve afterwards→keep an ice bath at hand). The resulting mixture is stirred under microwave irradiation at 100° C. for 10 min. After cooling the mixture to room temperature, the solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 25:75→0:100) to afford the title compound as an oil. Yield: 0.29 g (50% of theory); LC (method 1): tR=1.78 min; Mass spectrum (ESI+): m/z=198 [M+H]+. charged with a stir bar may evolve afterwards→keep an ice bath at hand After cooling the mixture to room temperature the solvent is evaporated the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 25:75→0:100)

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Propargylamine (0.21 mL) is added to a microwave oven suited vessel charged with a stir bar, 1-methyl-2-tetralone (0.50 mL), NaAuCl4*2H2O (27 mg), and ethanol (3 mL) (caution: a very exothermic reaction may evolve afterwards→keep an ice bath at hand). The resulting mixture is stirred under microwave irradiation at 100° C. for 10 min. After cooling the mixture to room temperature, the solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 25:75→0:100) to afford the title compound as an oil. Yield: 0.29 g (50% of theory); LC (method 1): tR=1.78 min; Mass spectrum (ESI+): m/z=198 [M+H]+. charged with a stir bar may evolve afterwards→keep an ice bath at hand After cooling the mixture to room temperature the solvent is evaporated the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 25:75→0:100)

Conditions: temp:-30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirring solution of diisopropylamine (4.81 mL, 34.3 mmol) in 50 mL of tetrahydrofuran cooled to 0° C. in an ice bath was added dropwise 1.6M n-butyl lithium in tetrahydrofuran (21.45 mL, 34.3 mmol) over 30 minutes. The solution was cooled to −30° C. and 1-methyl-2-tetralone (5.0 g, 31.2 mmol) in 10 mL of tetrahydrofuran added. The resulting reaction mixture was placed in an ice bath for 2 hour. Cool the solution to −78° C., and added hexamethylphosphoric triamide 20 mL followed by the dropwise addition of (2-Bromo-ethyl)-cyclopropane (6.97 g, 46.8 mmol). The reaction was stirred at rt for 48 hours. Partition the reaction mixture between ethyl acetate and saturated aqueous NH4Cl, extract the aqueous layer 3 times with ethyl acetate. The combined organic layers were washed sequentially with saturated sodium bicarbonate, brine, and then dried over MgSO4. The product was purified by flash chromatography on SiO2, eluting with a 0-10% diethyl ether/hexane gradient yielding the product (4.488 g, 63% yield). 1H NMR (300 MHz, CDCl3): δ ppm 0.01 (m, 2H) 0.47 (m, 2H) 0.67 (m, 1H) 0.98 (m, 2H) 1.55 (s, 3H) 1.95 (td, J=12.78, 4.60 Hz, 1H) 2.37 (ddd, J=13.60, 12.13, 4.78 Hz, 1H) 2.80 (m, 2H) 3.19 (m, 2H) 7.31 (m, 2H) 7.44 (m, 2H). MS (ESI+) m/z=229 (M+H)+. The resulting reaction mixture Cool the solution to −78° C. Partition the reaction mixture between ethyl acetate and saturated aqueous NH4Cl extract the aqueous layer 3 times with ethyl acetate The combined organic layers were washed sequentially with saturated sodium bicarbonate, brine dried over MgSO4 The product was purified by flash chromatography on SiO2 eluting with a 0-10% diethyl ether/hexane

Conditions: temp:-30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirring solution of diisopropylamine (4.81 mL, 34.3 mmol) in 50 mL of tetrahydrofuran cooled to 0° C. in an ice bath was added dropwise 1.6M n-butyl lithium in tetrahydrofuran (21.45 mL, 34.3 mmol) over 30 minutes. The solution was cooled to −30° C. and 1-methyl-2-tetralone (5.0 g, 31.2 mmol) in 10 mL of tetrahydrofuran added. The resulting reaction mixture was placed in an ice bath for 2 hour. Cool the solution to −78° C., and added hexamethylphosphoric triamide 20 mL followed by the dropwise addition of (2-Bromo-ethyl)-cyclopropane (6.97 g, 46.8 mmol). The reaction was stirred at rt for 48 hours. Partition the reaction mixture between ethyl acetate and saturated aqueous NH4Cl, extract the aqueous layer 3 times with ethyl acetate. The combined organic layers were washed sequentially with saturated sodium bicarbonate, brine, and then dried over MgSO4. The product was purified by flash chromatography on SiO2, eluting with a 0-10% diethyl ether/hexane gradient yielding the product (4.488 g, 63% yield). 1H NMR (300 MHz, CDCl3): δ ppm 0.01 (m, 2H) 0.47 (m, 2H) 0.67 (m, 1H) 0.98 (m, 2H) 1.55 (s, 3H) 1.95 (td, J=12.78, 4.60 Hz, 1H) 2.37 (ddd, J=13.60, 12.13, 4.78 Hz, 1H) 2.80 (m, 2H) 3.19 (m, 2H) 7.31 (m, 2H) 7.44 (m, 2H). MS (ESI+) m/z=229 (M+H)+. The resulting reaction mixture Cool the solution to −78° C. Partition the reaction mixture between ethyl acetate and saturated aqueous NH4Cl extract the aqueous layer 3 times with ethyl acetate The combined organic layers were washed sequentially with saturated sodium bicarbonate, brine dried over MgSO4 The product was purified by flash chromatography on SiO2 eluting with a 0-10% diethyl ether/hexane

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

Procedure: To a solution of 1-methyl-2-tetralone (10.0 g, 62.4 mmol), allyl acetate (7.42 mL, 68.7 mmol), cesium carbonate (20.3 g, 62.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.143 g, 0.156 mmol), 1,2-diaminocyclohexane-N,N′-bis(2′-diphenylphosphinobenzoyl) (0.215 g, 0.312 mmol) in tetrahydrofuran (300 mL) was bubbled a stream of nitrogen through the mixture for ten minutes. The solution was then stirred at room temperature for 4 days followed by the addition of ethyl acetate (200 mL) and a saturated aqueous solution of ammonium chloride. The organic layer was separated, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography employing 70-230 mesh silica gel eluting with a mixture of 10% ethyl acetate in hexane to provide the title compound as a light yellow oil (10.07 g, 90%). 1H NMR (300 MHz, CDCl3): δ 1.43 (s, 3H), 2.46 (m, 1H), 2.63 (m, 2H), 2.78 (m, 1H), 3.03 (m, 2H), 4.90 (m, 2H), 5.40 (m, 1H), 7.18 (m, 2H), 7.30 (m, 2H). The organic layer was separated dried (MgSO4) filtered concentrated in vacuo The residue was purified by column chromatography with a mixture of 10% ethyl acetate in hexane

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Propargylamine (0.21 mL) is added to a microwave oven suited vessel charged with a stir bar, 1-methyl-2-tetralone (0.50 mL), NaAuCl4*2H2O (27 mg), and ethanol (3 mL) (caution: a very exothermic reaction may evolve afterwards→keep an ice bath at hand). The resulting mixture is stirred under microwave irradiation at 100° C. for 10 min. After cooling the mixture to room temperature, the solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 25:75→0:100) to afford the title compound as an oil. Yield: 0.29 g (50% of theory); LC (method 1): tR=1.78 min; Mass spectrum (ESI+): m/z=198 [M+H]+. charged with a stir bar may evolve afterwards→keep an ice bath at hand After cooling the mixture to room temperature the solvent is evaporated the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 25:75→0:100)

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Propargylamine (0.21 mL) is added to a microwave oven suited vessel charged with a stir bar, 1-methyl-2-tetralone (0.50 mL), NaAuCl4*2H2O (27 mg), and ethanol (3 mL) (caution: a very exothermic reaction may evolve afterwards→keep an ice bath at hand). The resulting mixture is stirred under microwave irradiation at 100° C. for 10 min. After cooling the mixture to room temperature, the solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 25:75→0:100) to afford the title compound as an oil. Yield: 0.29 g (50% of theory); LC (method 1): tR=1.78 min; Mass spectrum (ESI+): m/z=198 [M+H]+. charged with a stir bar may evolve afterwards→keep an ice bath at hand After cooling the mixture to room temperature the solvent is evaporated the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 25:75→0:100)

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Propargylamine (0.21 mL) is added to a microwave oven suited vessel charged with a stir bar, 1-methyl-2-tetralone (0.50 mL), NaAuCl4*2H2O (27 mg), and ethanol (3 mL) (caution: a very exothermic reaction may evolve afterwards→keep an ice bath at hand). The resulting mixture is stirred under microwave irradiation at 100° C. for 10 min. After cooling the mixture to room temperature, the solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 25:75→0:100) to afford the title compound as an oil. Yield: 0.29 g (50% of theory); LC (method 1): tR=1.78 min; Mass spectrum (ESI+): m/z=198 [M+H]+. charged with a stir bar may evolve afterwards→keep an ice bath at hand After cooling the mixture to room temperature the solvent is evaporated the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 25:75→0:100)