Chlorocyclohexyldimethylsilane

反応条件: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a reaction container equipped with a dropping funnel, 24 g of 2,5-dibromopyridine and 270 ml of diethyl ether were added. The obtained solution was cooled at −70° C. and then, 62.93 mL of butyl lithium (1.61 M/hexane solution) was added dropwise thereto. The obtained mixture was stirred for 2 hours and then, a solution obtained by dissolving 18.75 mL of cyclohexyldimethylchlorosilane in 18.6 mL of diethyl ether was added dropwise thereto. The obtained mixture was stirred for 4 hours and then, 140 mL of water was added dropwise thereto at 0° C. The obtained mixture was stirred at room temperature overnight and then, 40 mL of water and 150 mL of diethyl ether were added thereto. The obtained solution was extracted three times with 150 mL of diethyl ether. The obtained organic layers were mixed and dried with magnesium sulfate. After removing magnesium sulfate by filtration, the filtrate was concentrated to obtain a crude product. The crude product was purified with silica gel column chromatography to obtain 23.0 g of 2-bromo-5-cyclohexyldimethylsilylpyridine. Purity: 93% (area percentage value obtained by gas chromatography analysis). To a reaction container equipped with a dropping funnel a solution obtained was added dropwise The obtained mixture was stirred for 4 hours at 0° C The obtained mixture was stirred at room temperature overnight The obtained solution was extracted three times with 150 mL of diethyl ether The obtained organic layers were mixed dried with magnesium sulfate After removing magnesium sulfate by filtration the filtrate was concentrated to obtain a crude product The crude product was purified with silica gel column chromatography

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

実験手順: A solution of cyclohexyldimethylchlorosilane (84.62 g, 478.7 mmol) and imidazole (32.59 g, 478.7 mmol) in DMF (300 mL) was reacted with 2-indanone (57.62 g, 436.0 mmol). The reaction mixture was stirred overnight at room temperature, treated with water (300 mL) and extracted with Et2O (3×200 mL). The combined organic phases were washed with water (3×300 mL) and dried over sodium sulfate. The solvents were removed to leave an orange oil. Distillation under reduced pressure gave 81.67 g (68.8%) of the title compound as a yellow oil (bp. 140-142° C./0.2 mbar). 1H NMR (CDCl3, δ): 7.25-7.11 (m, 3H); 7.01 (td, 3J=7.3 Hz, 4J=1.4 Hz, 1H); 5.76 (d, 4J=0.7 Hz, 1H); 3.29 (s, 2H) 1.77-1.74 (m, 5H); 1.27-1.13 (m, 5H); 0.90 (m, 1H); 0.24 (s, 6H). 13C NMR (CDCl3, δ): 162.44; 145.24; 136.60; 126.47; 123.07; 122.37; 118.91; 106.32; 39.52; 27.69; 26.77; 26.46; 26.33; −3.55. extracted with Et2O (3×200 mL) The combined organic phases were washed with water (3×300 mL) dried over sodium sulfate The solvents were removed to leave an orange oil Distillation under reduced pressure

反応条件: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a reaction container equipped with a dropping funnel, 24 g of 2,5-dibromopyridine and 270 ml of diethyl ether were added. The obtained solution was cooled at −70° C. and then, 62.93 mL of butyl lithium (1.61 M/hexane solution) was added dropwise thereto. The obtained mixture was stirred for 2 hours and then, a solution obtained by dissolving 18.75 mL of cyclohexyldimethylchlorosilane in 18.6 mL of diethyl ether was added dropwise thereto. The obtained mixture was stirred for 4 hours and then, 140 mL of water was added dropwise thereto at 0° C. The obtained mixture was stirred at room temperature overnight and then, 40 mL of water and 150 mL of diethyl ether were added thereto. The obtained solution was extracted three times with 150 mL of diethyl ether. The obtained organic layers were mixed and dried with magnesium sulfate. After removing magnesium sulfate by filtration, the filtrate was concentrated to obtain a crude product. The crude product was purified with silica gel column chromatography to obtain 23.0 g of 2-bromo-5-cyclohexyldimethylsilylpyridine. Purity: 93% (area percentage value obtained by gas chromatography analysis). To a reaction container equipped with a dropping funnel a solution obtained was added dropwise The obtained mixture was stirred for 4 hours at 0° C The obtained mixture was stirred at room temperature overnight The obtained solution was extracted three times with 150 mL of diethyl ether The obtained organic layers were mixed dried with magnesium sulfate After removing magnesium sulfate by filtration the filtrate was concentrated to obtain a crude product The crude product was purified with silica gel column chromatography

反応条件: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a reaction container equipped with a dropping funnel, 24 g of 2,5-dibromopyridine and 270 ml of diethyl ether were added. The obtained solution was cooled at −70° C. and then, 62.93 mL of butyl lithium (1.61 M/hexane solution) was added dropwise thereto. The obtained mixture was stirred for 2 hours and then, a solution obtained by dissolving 18.75 mL of cyclohexyldimethylchlorosilane in 18.6 mL of diethyl ether was added dropwise thereto. The obtained mixture was stirred for 4 hours and then, 140 mL of water was added dropwise thereto at 0° C. The obtained mixture was stirred at room temperature overnight and then, 40 mL of water and 150 mL of diethyl ether were added thereto. The obtained solution was extracted three times with 150 mL of diethyl ether. The obtained organic layers were mixed and dried with magnesium sulfate. After removing magnesium sulfate by filtration, the filtrate was concentrated to obtain a crude product. The crude product was purified with silica gel column chromatography to obtain 23.0 g of 2-bromo-5-cyclohexyldimethylsilylpyridine. Purity: 93% (area percentage value obtained by gas chromatography analysis). To a reaction container equipped with a dropping funnel a solution obtained was added dropwise The obtained mixture was stirred for 4 hours at 0° C The obtained mixture was stirred at room temperature overnight The obtained solution was extracted three times with 150 mL of diethyl ether The obtained organic layers were mixed dried with magnesium sulfate After removing magnesium sulfate by filtration the filtrate was concentrated to obtain a crude product The crude product was purified with silica gel column chromatography

反応条件: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a reaction container equipped with a dropping funnel, 24 g of 2,5-dibromopyridine and 270 ml of diethyl ether were added. The obtained solution was cooled at −70° C. and then, 62.93 mL of butyl lithium (1.61 M/hexane solution) was added dropwise thereto. The obtained mixture was stirred for 2 hours and then, a solution obtained by dissolving 18.75 mL of cyclohexyldimethylchlorosilane in 18.6 mL of diethyl ether was added dropwise thereto. The obtained mixture was stirred for 4 hours and then, 140 mL of water was added dropwise thereto at 0° C. The obtained mixture was stirred at room temperature overnight and then, 40 mL of water and 150 mL of diethyl ether were added thereto. The obtained solution was extracted three times with 150 mL of diethyl ether. The obtained organic layers were mixed and dried with magnesium sulfate. After removing magnesium sulfate by filtration, the filtrate was concentrated to obtain a crude product. The crude product was purified with silica gel column chromatography to obtain 23 g of 2-bromo-5-cyclohexyldimethylsilylpyridine. Purity: 93% (area percentage value obtained by gas chromatography analysis). To a reaction container equipped with a dropping funnel a solution obtained was added dropwise The obtained mixture was stirred for 4 hours at 0° C The obtained mixture was stirred at room temperature overnight The obtained solution was extracted three times with 150 mL of diethyl ether The obtained organic layers were mixed dried with magnesium sulfate After removing magnesium sulfate by filtration the filtrate was concentrated to obtain a crude product The crude product was purified with silica gel column chromatography

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

実験手順: 15.5 ml (25.2 mmol) of t-butyllithium are added dropwise at −80° C. to a solution of 2 g (8.4 mmol) of monoferrocenylacetamide in 40 ml of THF. The mixture is subsequently warmed slowly to room temperature. After stirring for one hour at room temperqture, an excess of cyclohexyldimethylchlorosilane is added [5 ml (23 mmol) of cyclohexyldimethylchlorosilane]. The mixture is poured into 100 ml of water and extracted a number of times with ether, and the combined ether phases are washed with water. Purification is carried out by means of column chromatography (eluant CH2Cl2; Al2O3). extracted a number of times with ether the combined ether phases are washed with water Purification

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

実験手順: A solution of cyclohexyldimethylchlorosilane (84.62 g, 478.7 mmol) and imidazole (32.59 g, 478.7 mmol) in DMF (300 mL) was reacted with 2-indanone (57.62 g, 436.0 mmol). The reaction mixture was stirred overnight at room temperature, treated with water (300 mL) and extracted with Et2O (3×200 mL). The combined organic phases were washed with water (3×300 mL) and dried over sodium sulfate. The solvents were removed to leave an orange oil. Distillation under reduced pressure gave 81.67 g (68.8%) of the title compound as a yellow oil (bp. 140-142° C./0.2 mbar). 1H NMR (CDCl3, δ): 7.25-7.11 (m, 3H); 7.01 (td, 3J=7.3 Hz, 4J=1.4 Hz, 1H); 5.76 (d, 4J=0.7 Hz, 1H); 3.29 (s, 2H) 1.77-1.74 (m, 5H); 1.27-1.13 (m, 5H); 0.90 (m, 1H); 0.24 (s, 6H). 13C NMR (CDCl3, δ): 162.44; 145.24; 136.60; 126.47; 123.07; 122.37; 118.91; 106.32; 39.52; 27.69; 26.77; 26.46; 26.33; −3.55. extracted with Et2O (3×200 mL) The combined organic phases were washed with water (3×300 mL) dried over sodium sulfate The solvents were removed to leave an orange oil Distillation under reduced pressure

反応条件: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a reaction container equipped with a dropping funnel, 24 g of 2,5-dibromopyridine and 270 ml of diethyl ether were added. The obtained solution was cooled at −70° C. and then, 62.93 mL of butyl lithium (1.61 M/hexane solution) was added dropwise thereto. The obtained mixture was stirred for 2 hours and then, a solution obtained by dissolving 18.75 mL of cyclohexyldimethylchlorosilane in 18.6 mL of diethyl ether was added dropwise thereto. The obtained mixture was stirred for 4 hours and then, 140 mL of water was added dropwise thereto at 0° C. The obtained mixture was stirred at room temperature overnight and then, 40 mL of water and 150 mL of diethyl ether were added thereto. The obtained solution was extracted three times with 150 mL of diethyl ether. The obtained organic layers were mixed and dried with magnesium sulfate. After removing magnesium sulfate by filtration, the filtrate was concentrated to obtain a crude product. The crude product was purified with silica gel column chromatography to obtain 23.0 g of 2-bromo-5-cyclohexyldimethylsilylpyridine. Purity: 93% (area percentage value obtained by gas chromatography analysis). To a reaction container equipped with a dropping funnel a solution obtained was added dropwise The obtained mixture was stirred for 4 hours at 0° C The obtained mixture was stirred at room temperature overnight The obtained solution was extracted three times with 150 mL of diethyl ether The obtained organic layers were mixed dried with magnesium sulfate After removing magnesium sulfate by filtration the filtrate was concentrated to obtain a crude product The crude product was purified with silica gel column chromatography