8-chloro-3,4-dihydro-2H-naphthalen-1-one

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

Procedure: 8.85 g of 8-chloro-1-tetralone were dissolved in 90 ml of tetrachloromethane under argon and added to 21.0 ml of 3-buten-2-ol and 190 mg of p-toluenesulfonic acid. The reaction solution was heated to reflux on a water separator for 9 days. The solvent was removed in a vacuum and the residue was chromatographed on 200 g of silica gel firstly with hexane/ethyl acetate 9:1 and then with hexane/ethyl acetate 4:1. In addition to large amounts of unreacted educt (8.3 g), there were obtained 4.1 g (35%) of 2-(2-buten-1-yl)-8-chloro-1-tetralone as a yellow oil. The reaction solution was heated The solvent was removed in a vacuum the residue was chromatographed on 200 g of silica gel firstly with hexane/ethyl acetate 9:1 In addition to large amounts of unreacted educt (8.3 g)

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

Procedure: 8.85 g of 8-chloro-1-tetralone were dissolved in 90 ml of tetrachloromethane under argon and added to 21.0 ml of 3-buten-2-ol and 190 mg of p-toluenesulfonic acid. The reaction solution was heated to reflux on a water separator for 9 days. The solvent was removed in a vacuum and the residue was chromatographed on 200 g of silica gel firstly with hexane/ethyl acetate 9:1 and then with hexane/ethyl acetate 4:1. In addition to large amounts of unreacted educt (8.3 g), there were obtained 4.1 g (35%) of 2-(2-buten-1-yl)-8-chloro-1-tetralone as a yellow oil. The reaction solution was heated The solvent was removed in a vacuum the residue was chromatographed on 200 g of silica gel firstly with hexane/ethyl acetate 9:1 In addition to large amounts of unreacted educt (8.3 g)

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

Procedure: A solution of 8-chloro-3,4-dihydronaphthalen-1(2H)-one (1.26 mmol) in MeOH (4 mL) at 0° C. was quickly charged with a solution of sodium borohydride (3.23 mmol, 2.5 eq) in MeOH (2 mL). The reaction was stirred for 1.5 h from 0° C. to ambient temperature. The reaction was quenched with water and extracted with ether. All organic layers were combined and dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude was dissolved in minimal CH2Cl2 and was purified by two rounds of pTLC [Silicycle, 20×20 plate, 1000 μm, one development in neat CH2Cl2], giving the title material as an off-white solid. 1H NMR (400 MHz, CDCl3) δ=1.72-1.85 (m, 2H), 1.92-2.05 (m, 1H), 2.16-2.24 (m, 1H), 2.38 (dd, J=3.8, 1.3 Hz, 1H), 2.71 (ddd, J=17.7, 12.1, 5.8 Hz, 1H), 2.82-2.92 (m, 1H), 5.09 (q, J=3.5 Hz, 1H), 7.06 (d, J=7.6 Hz, 1H), 7.15 (dd, J=7.7, 7.7 Hz, 1H), 7.24 (d, J=7.8 Hz, 1H). MS (ES+): m/z 164.98/166.98 (100/53) [MH+−H2O]. HPLC: tR=3.14 min (ZQ3, polar—5 min). The reaction was quenched with water extracted with ether dried over anhydrous Na2SO4 filtered concentrated in vacuo The crude was dissolved in minimal CH2Cl2 was purified by two rounds of pTLC [Silicycle, 20×20 plate, 1000 μm, one development in neat CH2Cl2]

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

Procedure: A solution of 8-chloro-3,4-dihydronaphthalen-1(2H)-one (1.26 mmol) in MeOH (4 mL) at 0° C. was quickly charged with a solution of sodium borohydride (3.23 mmol, 2.5 eq) in MeOH (2 mL). The reaction was stirred for 1.5 h from 0° C. to ambient temperature. The reaction was quenched with water and extracted with ether. All organic layers were combined and dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude was dissolved in minimal CH2Cl2 and was purified by two rounds of pTLC [Silicycle, 20×20 plate, 1000 μm, one development in neat CH2Cl2], giving the title material as an off-white solid. 1H NMR (400 MHz, CDCl3) δ=1.72-1.85 (m, 2H), 1.92-2.05 (m, 1H), 2.16-2.24 (m, 1H), 2.38 (dd, J=3.8, 1.3 Hz, 1H), 2.71 (ddd, J=17.7, 12.1, 5.8 Hz, 1H), 2.82-2.92 (m, 1H), 5.09 (q, J=3.5 Hz, 1H), 7.06 (d, J=7.6 Hz, 1H), 7.15 (dd, J=7.7, 7.7 Hz, 1H), 7.24 (d, J=7.8 Hz, 1H). MS (ES+): m/z 164.98/166.98 (100/53) [MH+−H2O]. HPLC: tR=3.14 min (ZQ3, polar—5 min). The reaction was quenched with water extracted with ether dried over anhydrous Na2SO4 filtered concentrated in vacuo The crude was dissolved in minimal CH2Cl2 was purified by two rounds of pTLC [Silicycle, 20×20 plate, 1000 μm, one development in neat CH2Cl2]

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

Procedure: 8.85 g of 8-chloro-1-tetralone were dissolved in 90 ml of tetrachloromethane under argon and added to 21.0 ml of 3-buten-2-ol and 190 mg of p-toluenesulfonic acid. The reaction solution was heated to reflux on a water separator for 9 days. The solvent was removed in a vacuum and the residue was chromatographed on 200 g of silica gel firstly with hexane/ethyl acetate 9:1 and then with hexane/ethyl acetate 4:1. In addition to large amounts of unreacted educt (8.3 g), there were obtained 4.1 g (35%) of 2-(2-buten-1-yl)-8-chloro-1-tetralone as a yellow oil. The reaction solution was heated The solvent was removed in a vacuum the residue was chromatographed on 200 g of silica gel firstly with hexane/ethyl acetate 9:1 In addition to large amounts of unreacted educt (8.3 g)

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

Procedure: A solution of 8-chloro-3,4-dihydronaphthalen-1(2H)-one (1.26 mmol) in MeOH (4 mL) at 0° C. was quickly charged with a solution of sodium borohydride (3.23 mmol, 2.5 eq) in MeOH (2 mL). The reaction was stirred for 1.5 h from 0° C. to ambient temperature. The reaction was quenched with water and extracted with ether. All organic layers were combined and dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude was dissolved in minimal CH2Cl2 and was purified by two rounds of pTLC [Silicycle, 20×20 plate, 1000 μm, one development in neat CH2Cl2], giving the title material as an off-white solid. 1H NMR (400 MHz, CDCl3) δ=1.72-1.85 (m, 2H), 1.92-2.05 (m, 1H), 2.16-2.24 (m, 1H), 2.38 (dd, J=3.8, 1.3 Hz, 1H), 2.71 (ddd, J=17.7, 12.1, 5.8 Hz, 1H), 2.82-2.92 (m, 1H), 5.09 (q, J=3.5 Hz, 1H), 7.06 (d, J=7.6 Hz, 1H), 7.15 (dd, J=7.7, 7.7 Hz, 1H), 7.24 (d, J=7.8 Hz, 1H). MS (ES+): m/z 164.98/166.98 (100/53) [MH+−H2O]. HPLC: tR=3.14 min (ZQ3, polar—5 min). The reaction was quenched with water extracted with ether dried over anhydrous Na2SO4 filtered concentrated in vacuo The crude was dissolved in minimal CH2Cl2 was purified by two rounds of pTLC [Silicycle, 20×20 plate, 1000 μm, one development in neat CH2Cl2]

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

Procedure: 8.85 g of 8-chloro-1-tetralone were dissolved in 90 ml of tetrachloromethane under argon and added to 21.0 ml of 3-buten-2-ol and 190 mg of p-toluenesulfonic acid. The reaction solution was heated to reflux on a water separator for 9 days. The solvent was removed in a vacuum and the residue was chromatographed on 200 g of silica gel firstly with hexane/ethyl acetate 9:1 and then with hexane/ethyl acetate 4:1. In addition to large amounts of unreacted educt (8.3 g), there were obtained 4.1 g (35%) of 2-(2-buten-1-yl)-8-chloro-1-tetralone as a yellow oil. The reaction solution was heated The solvent was removed in a vacuum the residue was chromatographed on 200 g of silica gel firstly with hexane/ethyl acetate 9:1 In addition to large amounts of unreacted educt (8.3 g)