6-chloro-2,3-dihydroinden-1-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A solution of 20.2 g of 6-chloro-1-indanone, 25 ml of 3-buten-2-ol and 200 mg of p-toluenesulfonic acid in 25 ml of 2,2-dimethoxypropane and 200 ml of anhydrous toluene was boiled under reflux for 16 hours. The reaction mixture was subsequently concentrated in a vacuum and purified by column chromatography on silica gel (hexane/diethyl ether 5:1). 10.3 g (39%) of (RS)-2-(2-buten-1-yl)-6-chloro-1-indanone were obtained as a yellow oil. under reflux for 16 hours The reaction mixture was subsequently concentrated in a vacuum purified by column chromatography on silica gel (hexane/diethyl ether 5:1)

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

Procedure: A solution of 20.2 g of 6-chloro-1-indanone, 25 ml of 3-buten-2-ol and 200 mg of p-toluenesulfonic acid in 25 ml of 2,2-dimethoxypropane and 200 ml of anhydrous toluene was boiled under reflux for 16 hours. The reaction mixture was subsequently concentrated in a vacuum and purified by column chromatography on silica gel (hexane/diethyl ether 5:1). 10.3 g (39%) of (RS)-2-(2-buten-1-yl)-6-chloro-1-indanone were obtained as a yellow oil. under reflux for 16 hours The reaction mixture was subsequently concentrated in a vacuum purified by column chromatography on silica gel (hexane/diethyl ether 5:1)

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

Procedure: To a solution of 6-chloro-1-indanone (II) (100.0 g, 600.2 mmol) in 1,2-dichloroethane (1.00 L) was added 2,2′-azo-bis-isobutyronitrile (9.86 g, 60.0 mmol) followed by N-bromosuccinimide (224.3 g, 1.26 mol). The reaction mixture was quickly heated to reflux. After 30 min at reflux, more 2,2′-azo-bis-isobutyronitrile (9.86 g, 60.0 mmol) was added. The reaction mixture was kept for 4.5 h at reflux. Afterwards the mixture was stirred at room temperature overnight. The mixture was cooled to 0° C., and triethylamine (126 mL, 904 mmol) was added dropwise. The mixture was stirred for 1 h at 0° C., and then allowed to heat to room temperature. Water (1.0 L) was added. The mixture was vigorously stirred for 15 min. The stirring was stopped, and the aqueous layer was removed by suction. Fresh water (1.0 L) was added, and the mixture was stirred for 15 min. The aqueous layer was then separated by suction. The organic phase was further shaken with brine (500 mL) in a separating funnel. The reaction mixture was quickly heated to reflux After 30 min at reflux at reflux The mixture was cooled to 0° C. The mixture was stirred for 1 h at 0° C. to heat to room temperature The mixture was vigorously stirred for 15 min the aqueous layer was removed by suction Fresh water (1.0 L) was added the mixture was stirred for 15 min The aqueous layer was then separated by suction The organic phase was further shaken with brine (500 mL) in a separating funnel

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

Procedure: 45 ml (22.5 mmol) of a 0.5N solution of cyclopropylmagnesium bromide in tetrahydrofuran were added to 2.50 g (15.0 mmol) of a mixture of 5-chloro-2,3-dihydro-1H-inden-1-one and 6-chloro-2,3-dihydro-1H-inden-1-one in 56 ml of diethyl ether at RT, and the mixture was stirred at RT overnight. The reaction mixture was added to ice-water, the phases were separated, the aqueous phase was extracted with dichloromethane, and the combined organic phases were dried over magnesium sulfate, filtered and concentrated. The crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient) and preparative HPLC (mobile phase: acetonitrile/water gradient) to result in 152 mg (5% of theory) of the title compound. the phases were separated the aqueous phase was extracted with dichloromethane the combined organic phases were dried over magnesium sulfate filtered concentrated The crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient) and preparative HPLC (mobile phase: acetonitrile/water gradient)

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

Procedure: 45 ml (22.5 mmol) of a 0.5N solution of cyclopropylmagnesium bromide in tetrahydrofuran were added to 2.50 g (15.0 mmol) of a mixture of 5-chloro-2,3-dihydro-1H-inden-1-one and 6-chloro-2,3-dihydro-1H-inden-1-one in 56 ml of diethyl ether at RT, and the mixture was stirred at RT overnight. The reaction mixture was added to ice-water, the phases were separated, the aqueous phase was extracted with dichloromethane, and the combined organic phases were dried over magnesium sulfate, filtered and concentrated. The crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient) and preparative HPLC (mobile phase: acetonitrile/water gradient) to result in 71.0 mg (2% of theory) of a mixture of 5-chloro-1-cyclopropyl-2,3-dihydro-1H-inden-1-ol and 6-chloro-1-cyclopropyl-2,3-dihydro-1H-inden-1-ol. the phases were separated the aqueous phase was extracted with dichloromethane the combined organic phases were dried over magnesium sulfate filtered concentrated The crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient) and preparative HPLC (mobile phase: acetonitrile/water gradient)

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

Procedure: 45 ml (22.5 mmol) of a 0.5N solution of cyclopropylmagnesium bromide in tetrahydrofuran were added to 2.50 g (15.0 mmol) of a mixture of 5-chloro-2,3-dihydro-1H-inden-1-one and 6-chloro-2,3-dihydro-1H-inden-1-one in 56 ml of diethyl ether at RT, and the mixture was stirred at RT overnight. The reaction mixture was added to ice-water, the phases were separated, the aqueous phase was extracted with dichloromethane, and the combined organic phases were dried over magnesium sulfate, filtered and concentrated. The crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient) and preparative HPLC (mobile phase: acetonitrile/water gradient) to result in 71.0 mg (2% of theory) of a mixture of 5-chloro-1-cyclopropyl-2,3-dihydro-1H-inden-1-ol and 6-chloro-1-cyclopropyl-2,3-dihydro-1H-inden-1-ol. the phases were separated the aqueous phase was extracted with dichloromethane the combined organic phases were dried over magnesium sulfate filtered concentrated The crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient) and preparative HPLC (mobile phase: acetonitrile/water gradient)

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

Procedure: A solution of 20.2 g of 6-chloro-1-indanone, 25 ml of 3-buten-2-ol and 200 mg of p-toluenesulfonic acid in 25 ml of 2,2-dimethoxypropane and 200 ml of anhydrous toluene was boiled under reflux for 16 hours. The reaction mixture was subsequently concentrated in a vacuum and purified by column chromatography on silica gel (hexane/diethyl ether 5:1). 10.3 g (39%) of (RS)-2-(2-buten-1-yl)-6-chloro-1-indanone were obtained as a yellow oil. under reflux for 16 hours The reaction mixture was subsequently concentrated in a vacuum purified by column chromatography on silica gel (hexane/diethyl ether 5:1)

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

Procedure: A solution of 9.59 g (60.0 mmoles) of bromine in 20 ml of acetic acid ethyl ester is added dropwise to a solution of 10.0 g (60.0 mmoles) of 6-chloro-1-indanone in 80 ml of acetic acid ethyl ester and 0.5 ml of 48% strength aqueous hydrobromic acid. After stirring for 3 hours, the reaction solution is concentrated to dryness, the residue is stirred with 50 ml of water and the precipitate is filtered off. The crude product of melting point 84°-87° is recrystallized from petroleum ether 60/70 and gives the pure product of melting point 92°-94° C. the reaction solution is concentrated to dryness the residue is stirred with 50 ml of water the precipitate is filtered off The crude product of melting point 84°-87° is recrystallized from petroleum ether 60/70 gives the pure product of melting point 92°-94° C.