1-ethyl-1H-indene

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

Procedure: A 500 mL three-neck flask replaced with nitrogen was charged with 21.6 g (purity 72%, 42 mmol) of the yellow oily product and 274 mL of tetrahydrofuran, and cooled in an ice bath, and then 88.5 mL (1.59 M, 141 mmol) of a hexane solution of n-butyllithium was added dropwise. The color of the solution was turned from colorless to yellow. The temperature of this solution was gradually raised to room temperature, and the solution was further stirred for 1 hour. While this solution was cooled in a water bath, 137 mL of distilled water was added dropwise. After the organic layer was separated, the aqueous layer was extracted with ethyl acetate. The separated organic layer and the extract were combined, washed with an aqueous saturated sodium chloride solution two times, and dried with sodium sulfate. Volatile components were distilled off under reduced pressure, and the resulting yellow oily product was purified by column chromatography (developing solvent: heptane/methylene chloride v/v=9/1), and recrystallized with ethanol/methylene chloride. Based on the following 1H NMR (400 MHz, CDCl3) data, the resulting pale yellow solid was identified to be (5,6,7,8-tetrahydro-5,5,8,8-tetramethylbenz-f-inden-3-yl) (inden-3-yl)ethane. Yield amount 9.1 g (purity>98%, 24 mmol, yield 57%). A 500 mL three-neck flask replaced with nitrogen cooled in an ice bath While this solution was cooled in a water bath After the organic layer was separated the aqueous layer was extracted with ethyl acetate washed with an aqueous saturated sodium chloride solution two times dried with sodium sulfate Volatile components were distilled off under reduced pressure the resulting yellow oily product was purified by column chromatography ( heptane/methylene chloride v/v=9/1), and recrystallized with ethanol/methylene chloride Yield amount 9.1 g (purity>98%, 24 mmol, yield 57%)

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

Procedure: A 500 mL three-neck flask replaced with nitrogen was charged with 21.6 g (purity 72%, 42 mmol) of the yellow oily product and 274 mL of tetrahydrofuran, and cooled in an ice bath, and then 88.5 mL (1.59 M, 141 mmol) of a hexane solution of n-butyllithium was added dropwise. The color of the solution was turned from colorless to yellow. The temperature of this solution was gradually raised to room temperature, and the solution was further stirred for 1 hour. While this solution was cooled in a water bath, 137 mL of distilled water was added dropwise. After the organic layer was separated, the aqueous layer was extracted with ethyl acetate. The separated organic layer and the extract were combined, washed with an aqueous saturated sodium chloride solution two times, and dried with sodium sulfate. Volatile components were distilled off under reduced pressure, and the resulting yellow oily product was purified by column chromatography (developing solvent: heptane/methylene chloride v/v=9/1), and recrystallized with ethanol/methylene chloride. Based on the following 1H NMR (400 MHz, CDCl3) data, the resulting pale yellow solid was identified to be (5,6,7,8-tetrahydro-5,5,8,8-tetramethylbenz-f-inden-3-yl) (inden-3-yl)ethane. Yield amount 9.1 g (purity>98%, 24 mmol, yield 57%). A 500 mL three-neck flask replaced with nitrogen cooled in an ice bath While this solution was cooled in a water bath After the organic layer was separated the aqueous layer was extracted with ethyl acetate washed with an aqueous saturated sodium chloride solution two times dried with sodium sulfate Volatile components were distilled off under reduced pressure the resulting yellow oily product was purified by column chromatography ( heptane/methylene chloride v/v=9/1), and recrystallized with ethanol/methylene chloride Yield amount 9.1 g (purity>98%, 24 mmol, yield 57%)

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

Procedure: A 500 mL three-neck flask replaced with nitrogen was charged with 21.6 g (purity 72%, 42 mmol) of the yellow oily product and 274 mL of tetrahydrofuran, and cooled in an ice bath, and then 88.5 mL (1.59 M, 141 mmol) of a hexane solution of n-butyllithium was added dropwise. The color of the solution was turned from colorless to yellow. The temperature of this solution was gradually raised to room temperature, and the solution was further stirred for 1 hour. While this solution was cooled in a water bath, 137 mL of distilled water was added dropwise. After the organic layer was separated, the aqueous layer was extracted with ethyl acetate. The separated organic layer and the extract were combined, washed with an aqueous saturated sodium chloride solution two times, and dried with sodium sulfate. Volatile components were distilled off under reduced pressure, and the resulting yellow oily product was purified by column chromatography (developing solvent: heptane/methylene chloride v/v=9/1), and recrystallized with ethanol/methylene chloride. Based on the following 1H NMR (400 MHz, CDCl3) data, the resulting pale yellow solid was identified to be (5,6,7,8-tetrahydro-5,5,8,8-tetramethylbenz-f-inden-3-yl) (inden-3-yl)ethane. Yield amount 9.1 g (purity>98%, 24 mmol, yield 57%). A 500 mL three-neck flask replaced with nitrogen cooled in an ice bath While this solution was cooled in a water bath After the organic layer was separated the aqueous layer was extracted with ethyl acetate washed with an aqueous saturated sodium chloride solution two times dried with sodium sulfate Volatile components were distilled off under reduced pressure the resulting yellow oily product was purified by column chromatography ( heptane/methylene chloride v/v=9/1), and recrystallized with ethanol/methylene chloride Yield amount 9.1 g (purity>98%, 24 mmol, yield 57%)

Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 30 ml (0.26 moles) of indene in 250 ml of THF, 105 ml is added (0.26 moles) of 2.5 M BuLi in hexane, with temperature being kept comprised within the range of from 30° C. to 40° C. The reaction mixture is then cooled down to -70° C. and 19 ml (0.25 moles) of ethyl bromide is added dropwise during approximately 3 hours. The temperature is allowed to rise up to approximately 20-25° C. and then the mixture is hydrolysed with water and extracted with petroleum ether. After washing until neutral, drying and evaporation of the organic phase, the obtained residue is distilled. The fraction boiling at 92-95° C./30 mm Hg is collected, and 28 g of 1-ethylindene is obtained (yield 78%) being kept comprised within the range of from 30° C. to 40° C to rise up to approximately 20-25° C. extracted with petroleum ether After washing until neutral, drying evaporation of the organic phase the obtained residue is distilled The fraction boiling at 92-95° C./30 mm Hg is collected

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

Procedure: A 500 mL three-neck flask replaced with nitrogen was charged with 21.6 g (purity 72%, 42 mmol) of the yellow oily product and 274 mL of tetrahydrofuran, and cooled in an ice bath, and then 88.5 mL (1.59 M, 141 mmol) of a hexane solution of n-butyllithium was added dropwise. The color of the solution was turned from colorless to yellow. The temperature of this solution was gradually raised to room temperature, and the solution was further stirred for 1 hour. While this solution was cooled in a water bath, 137 mL of distilled water was added dropwise. After the organic layer was separated, the aqueous layer was extracted with ethyl acetate. The separated organic layer and the extract were combined, washed with an aqueous saturated sodium chloride solution two times, and dried with sodium sulfate. Volatile components were distilled off under reduced pressure, and the resulting yellow oily product was purified by column chromatography (developing solvent: heptane/methylene chloride v/v=9/1), and recrystallized with ethanol/methylene chloride. Based on the following 1H NMR (400 MHz, CDCl3) data, the resulting pale yellow solid was identified to be (5,6,7,8-tetrahydro-5,5,8,8-tetramethylbenz-f-inden-3-yl) (inden-3-yl)ethane. Yield amount 9.1 g (purity>98%, 24 mmol, yield 57%). A 500 mL three-neck flask replaced with nitrogen cooled in an ice bath While this solution was cooled in a water bath After the organic layer was separated the aqueous layer was extracted with ethyl acetate washed with an aqueous saturated sodium chloride solution two times dried with sodium sulfate Volatile components were distilled off under reduced pressure the resulting yellow oily product was purified by column chromatography ( heptane/methylene chloride v/v=9/1), and recrystallized with ethanol/methylene chloride Yield amount 9.1 g (purity>98%, 24 mmol, yield 57%)