2-cyclohexyl-2-methylpropanal

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A suspension of p-chlorobenzamide (5.31 g, 35.10 mmol), 2-cyclohexyl-2-methylpropanal (4.5 g, 35.10 mmol), and benzotriazole (4.18 g, 35.10 mmol) in toluene (100 mL) was treated with p-toluenesulfonic acid (334 mg, 1.76 mmol). The solution was heated at reflux under Dean-Stark conditions for 10 hours, then cooled gradually to ambient temperature. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (elution with 10% EtOAc/hexane) to provide 5.3 g of the desired product as a white solid. The solution was heated at reflux under Dean-Stark conditions for 10 hours The solvent was removed under reduced pressure the residue was purified by flash chromatography (elution with 10% EtOAc/hexane)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A suspension of p-chlorobenzamide (5.31 g, 35.10 mmol), 2-cyclohexyl-2-methylpropanal (4.5 g, 35.10 mmol), and benzotriazole (4.18 g, 35.10 mmol) in toluene (100 mL) was treated with p-toluenesulfonic acid (334 mg, 1.76 mmol). The solution was heated at reflux under Dean-Stark conditions for 10 hours, then cooled gradually to ambient temperature. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (elution with 10% EtOAc/hexane) to provide 5.3 g of the desired product as a white solid. The solution was heated at reflux under Dean-Stark conditions for 10 hours The solvent was removed under reduced pressure the residue was purified by flash chromatography (elution with 10% EtOAc/hexane)

反応条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Oxalyl chloride (7.8 g, 61.42 mmol) in methylene chloride (60 mL) at −78° C. was treated with dimethylsufoxide (8.4 g, 107.5 mmol). After stirring at −78° C. for 10 minutes, the mixture was treated with 2-cyclohexyl-2-methylpropanol (4.8 g, 36.86 mmol) in 15 ml of methylene chloride. The mixture was allowed to stir at −78° C. for 30 minutes and then treated with triethylamine (15.54 g, 153.6 mmol). The reaction mixture was stirred for 10 minutes and then stirred an additional 5 minutes at 0° C. The mixture was quenched with saturated aqueous ammonium (10 mL) chloride and extracted with diethyl ether (2×50 mL). The organic layer was washed with brine (15 mL), dried over anhydrous sodium sulfate and concentrated under vacuo. The crude product was redissolved in diethyl ether and the resulting precipitate was filtered through a pad of Celite. The solution was concentrated under reduced pressure to provide 4.5 g of 2-cyclohexyl-2-methylpropanal as an oil. to stir at −78° C. for 30 minutes The reaction mixture was stirred for 10 minutes stirred an additional 5 minutes at 0° C The mixture was quenched with saturated aqueous ammonium (10 mL) chloride extracted with diethyl ether (2×50 mL) The organic layer was washed with brine (15 mL) dried over anhydrous sodium sulfate concentrated under vacuo The crude product was redissolved in diethyl ether the resulting precipitate was filtered through a pad of Celite The solution was concentrated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The product from Example 22A, 4-chlorobenzamide, benzotriazole, and p-toluenesulfonic acid were processed as described in Example 1C to provide the title compound.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The product from Example 22A, 4-chlorobenzamide, benzotriazole, and p-toluenesulfonic acid were processed as described in Example 1C to provide the title compound.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-Cyclohexyl-2-methyl-1-propanol, oxalyl chloride and dimethylsulfoxide were processed as described in Example 18A to provide the title compound.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A suspension of p-chlorobenzamide (5.31 g, 35.10 mmol), 2-cyclohexyl-2-methylpropanal (4.5 g, 35.10 mmol), and benzotriazole (4.18 g, 35.10 mmol) in toluene (100 mL) was treated with p-toluenesulfonic acid (334 mg, 1.76 mmol). The solution was heated at reflux under Dean-Stark conditions for 10 hours, then cooled gradually to ambient temperature. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (elution with 10% EtOAc/hexane) to provide 5.3 g of the desired product as a white solid. The solution was heated at reflux under Dean-Stark conditions for 10 hours The solvent was removed under reduced pressure the residue was purified by flash chromatography (elution with 10% EtOAc/hexane)

反応条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Oxalyl chloride (7.8 g, 61.42 mmol) in methylene chloride (60 mL) at −78° C. was treated with dimethylsufoxide (8.4 g, 107.5 mmol). After stirring at −78° C. for 10 minutes, the mixture was treated with 2-cyclohexyl-2-methylpropanol (4.8 g, 36.86 mmol) in 15 ml of methylene chloride. The mixture was allowed to stir at −78° C. for 30 minutes and then treated with triethylamine (15.54 g, 153.6 mmol). The reaction mixture was stirred for 10 minutes and then stirred an additional 5 minutes at 0° C. The mixture was quenched with saturated aqueous ammonium (10 mL) chloride and extracted with diethyl ether (2×50 mL). The organic layer was washed with brine (15 mL), dried over anhydrous sodium sulfate and concentrated under vacuo. The crude product was redissolved in diethyl ether and the resulting precipitate was filtered through a pad of Celite. The solution was concentrated under reduced pressure to provide 4.5 g of 2-cyclohexyl-2-methylpropanal as an oil. to stir at −78° C. for 30 minutes The reaction mixture was stirred for 10 minutes stirred an additional 5 minutes at 0° C The mixture was quenched with saturated aqueous ammonium (10 mL) chloride extracted with diethyl ether (2×50 mL) The organic layer was washed with brine (15 mL) dried over anhydrous sodium sulfate concentrated under vacuo The crude product was redissolved in diethyl ether the resulting precipitate was filtered through a pad of Celite The solution was concentrated under reduced pressure