1-propan-2-ylideneindene

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

Procedure: 18.8 cm3 (47.0 mmol) of n-butyllithium were added at 0° C. to a solution of 5.93 g (47.0 mmol) of indene (industrial, 91% pure) filtered over Al2O3. After the mixture had been stirred at room temperature for 15 minutes, the solution was slowly added dropwise to a solution of 7.40 g (47.0 mmol) of 1-isopropylideneindene. After the mixture had been stirred at room temperature for 2 hours, 50 cm3 of water were added and the mixture was extracted with diethyl ether. The yellow organic phase was dried over MgSO4. The residue which remained after the solvent had been stripped off was chromatographed on silica gel 60. 1.5 g (13%) of the product (2 isomers) could be isolated with hexane/methylene chloride (10:1). filtered over Al2O3 After the mixture had been stirred at room temperature for 2 hours the mixture was extracted with diethyl ether The yellow organic phase was dried over MgSO4 was chromatographed on silica gel 60

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 1.58 g 2-methyl-1-phenyl-1H-imidazole (10 mmol) in 15 ml of tetrahydrofuran was cooled to −78° C. and 6.25 ml of 15% n-butyl-lithium in hexane (10 mmol) were added. The resulting mixture was stirred for an additional 20 min and then treated with a solution of 1.56 g 1-(1-methylethylidene)-1H-indene (10 mmol) in 5 ml tetrahydrofuran with vigorous stirring while the temperature was maintained at −78° C. The reaction mixture was allowed to reach room temperature, stirred for 14 h and hydrolyzed with saturated ammonium chloride solution. The organic layer was isolated and the aqueous layer was extracted three times with dichloromethane. The organic layers were dried over MgSO4, filtered and the solvent removed. The crude product was purified by column chromatography with silica as stationary phase. At the beginning a 5/1 hexane/ethyl acetate elution mixture was used (for the separation from 1-(1-methylethylidene)-1H-indene). Then, the elution mixture was changed to 1/1 hexane/ethyl acetate. After removal of the solvent 2.13 g (69%) of 2-[2-(1H-inden-3-yl)-2-methylpropyl]-1-phenyl-1H-imidazole was obtained as an oil. with vigorous stirring while the temperature to reach room temperature The organic layer was isolated the aqueous layer was extracted three times with dichloromethane The organic layers were dried over MgSO4 filtered the solvent removed The crude product was purified by column chromatography with silica as stationary phase At the beginning a 5/1 hexane/ethyl acetate elution mixture for the separation from 1-(1-methylethylidene)-1H-indene) After removal of the solvent 2.13 g (69%) of 2-[2-(1H-inden-3-yl)-2-methylpropyl]-1-phenyl-1H-imidazole was obtained as an oil

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2,4-dimethyl-1,3-thiazole (3.2 g, 28.1 mmol) in 20 ml of tetrahydrofuran was cooled to −78° C. and 15% n-butyl-lithium in hexane (17.5 ml, 28 mmol) was added during 15 min with stirring. The resulting yellow suspension was stirred for 20 min and then a solution of 1-(1-methylethylidene)-1H-indene (4.6 g, 29 mmol) in 5 ml of tetrahydrofuran added with vigorous stirring while the temperature was maintained at −78° C. The reaction mixture was allowed to reach room temperature and for 14 h. The resulting mixture was hydrolyzed with a saturated ammonium chloride solution. The resulting yellow suspension was stirred for 20 min with vigorous stirring while the temperature

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

Procedure: A solution of α-Picoline (1.97 ml, 20 mmol) in 10 ml of tetrahydrofuran was cooled to −20° C. and 15% n-butyl-lithium in hexane (13 ml, 20 mmol) was added during 10 min with stirring. The cooling bath was removed and the solution allowed to stir for 1 h while the temperature rose to room temperature. The resulting mixture was treated with a solution of 1-(1-methylethylidene)-1H-indene (3.12 g, 20 mmol) in 5 ml of tetrahydrofuran (5 ml) with vigorous stirring. The resulting solution was stirred for 14 h and hydrolyzed with 60 ml of 15-% hydrochloric acid. The organic layer was isolated and the aqueous phase washed once with ethyl acetate, then neutralized with aqueous ammonia solution and extracted three times with dichloromethane. The combined organic layers were dried over MgSO4, filtered and the solvent removed to give 4.28 g (86%) of 2-[2-(1H-inden-1-yl)-2-methylpropyl]pyridine as an oil. The product was NMR-pure, so no further distillation was necessary. The cooling bath was removed to stir for 1 h while the temperature rose to room temperature The organic layer was isolated the aqueous phase washed once with ethyl acetate extracted three times with dichloromethane The combined organic layers were dried over MgSO4 filtered the solvent removed

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

Procedure: 18.8 cm3 (47.0 mmol) of n-butyllithium were added at 0° C. to a solution of 5.93 g (47.0 mmol) of indene (industrial, 91% pure) filtered over Al2O3. After the mixture had been stirred at room temperature for 15 minutes, the solution was slowly added dropwise to a solution of 7.40 g (47.0 mmol) of 1-isopropylideneindene. After the mixture had been stirred at room temperature for 2 hours, 50 cm3 of water were added and the mixture was extracted with diethyl ether. The yellow organic phase was dried over MgSO4. The residue which remained after the solvent had been stripped off was chromatographed on silica gel 60. 1.5 g (13%) of the product (2 isomers) could be isolated with hexane/methylene chloride (10:1). filtered over Al2O3 After the mixture had been stirred at room temperature for 2 hours the mixture was extracted with diethyl ether The yellow organic phase was dried over MgSO4 was chromatographed on silica gel 60

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

Procedure: 18.8 cm3 (47.0 mmol) of n-butyllithium were added at 0° C. to a solution of 5.93 g (47.0 mmol) of indene (industrial, 91% pure) filtered over Al2O3. After the mixture had been stirred at room temperature for 15 minutes, the solution was slowly added dropwise to a solution of 7.40 g (47.0 mmol) of 1-isopropylideneindene. After the mixture had been stirred at room temperature for 2 hours, 50 cm3 of water were added and the mixture was extracted with diethyl ether. The yellow organic phase was dried over MgSO4. The residue which remained after the solvent had been stripped off was chromatographed on silica gel 60. 1.5 g (13%) of the product (2 isomers) could be isolated with hexane/methylene chloride (10:1). filtered over Al2O3 After the mixture had been stirred at room temperature for 2 hours the mixture was extracted with diethyl ether The yellow organic phase was dried over MgSO4 was chromatographed on silica gel 60