2,3-二氢-2-甲基-1H-苯并[E]茚-1-酮

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 2-methyl-2,3-dihydro-1H-cyclopenta[a]naphtalen-1-one (28.09 g, 0.143 mol) in 100 mL of THF was slowly added to a suspension of LiAlH4 (2.18 g, 58 mmol) in 200 mL of ether and refluxed for 2 h under stirring. The reaction mixture was subsequently transferred into a 2-L beaker and slowly hydrolyzed, under constant stirring, by dropwise addition of a 10% aq. solution of HCl until pH 5. The organic layer was separated, while the water layer was extracted with ether (3×100 mL). The organic layers were collected, washed with potassium carbonate/water until neutral pH, dried over MgSO4 and evaporated off to dryness. The so-obtained product, as a mixture of two isomers, was used in the next step without further purification. refluxed for 2 h The organic layer was separated, while the water layer was extracted with ether (3×100 mL) The organic layers were collected washed with potassium carbonate/water until neutral pH dried over MgSO4 evaporated off to dryness The so-obtained product, as a mixture of two isomers was used in the next step without further purification

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 2-methyl-2,3-dihydro-1H-cyclopenta[a]naphtalen-1-one (28.09 g, 0.143 mol) in 100 mL of THF was slowly added to a suspension of LiAlH4 (2.18 g, 58 mmol) in 200 mL of ether and refluxed for 2 h under stirring. The reaction mixture was subsequently transferred into a 2-L beaker and slowly hydrolyzed, under constant stirring, by dropwise addition of a 10% aq. solution of HCl until pH 5. The organic layer was separated, while the water layer was extracted with ether (3×100 mL). The organic layers were collected, washed with potassium carbonate/water until neutral pH, dried over MgSO4 and evaporated off to dryness. The so-obtained product, as a mixture of two isomers, was used in the next step without further purification. refluxed for 2 h The organic layer was separated, while the water layer was extracted with ether (3×100 mL) The organic layers were collected washed with potassium carbonate/water until neutral pH dried over MgSO4 evaporated off to dryness The so-obtained product, as a mixture of two isomers was used in the next step without further purification

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Sodium borohydride (7.5 g) was added portion-wise at 0-20° C. to a solution of 18.1 g of 2,3-dihydro-2-methyl-benz[e]indene-1-one in 200 ml of methanol. The reaction was completed after 15 min of stirring, and the reaction mixture was poured into 400 ml of water. The organic layer was separated, and the water layer was extracted with diethyl ether. The combined organic layers were washed with water and brine, dried over magnesium sulfate, and evaporated to dryness. The crude product was recrystallized from cyclohexane to obtain 14.3 g (78%) of 2,3-dihydro-1-hydroxy-2-methyl-1H-benz[e]indene. The organic layer was separated the water layer was extracted with diethyl ether The combined organic layers were washed with water and brine dried over magnesium sulfate evaporated to dryness The crude product was recrystallized from cyclohexane

反应条件: temp:-30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Aluminum chloride powder (240 g) was added to a dry round-bottomed flask under nitrogen, after which 1 l of dichloromethane was added. The suspension was cooled to -30° C., and 100 g of naphthalene and 90.5 g of freshly distilled 2-methyl-2-propenoyl chloride in 950 ml of dichloromethane were added dropwise under nitrogen in 1.5 h. The reaction mixture was stirred for another hour at -30° C., after which the cold reaction mixture was poured into 10 l of ice water. The organic layer was separated, the water layer was extracted with dichloromethane, and the combined organic layers were washed with brine, dried over magnesium sulfate, and evaporated to dryness. The crude product was distilled at 200° C./33 Pa, after which 127 g (84%) of 2,3-dihydro-2-methyl-1H-benz[e]indene-1-one were obtained with a purity >95% (GLC). after which the cold reaction mixture The organic layer was separated the water layer was extracted with dichloromethane the combined organic layers were washed with brine dried over magnesium sulfate evaporated to dryness The crude product was distilled at 200° C./33 Pa

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Aluminium chloride (35 g, 0.26 mole) was suspended in 200 ml of anhydrous dichioromethane. 2-Chloro-2-methyl-1-(1-naphthalenyl)-1-propanone (30.0 g, 0.13 mole) in 30 ml of heptane was slowly added to this suspension. During the addition (30 min) the temperature was kept at room temperature. After the addition was completed, the reaction mixture was stirred for 1 h at room temperature. The reaction mixture was poured onto 400 g of ice water, and the organic layer was separated. The organic layer was successively washed twice with a 5 wt % aqueous hydrochloric acid solution (150 ml) and once with a 2 wt % aqueous sodium bicarbonate solution (150 ml). After drying over anhydrous magnesium sulfate the solution was concentrated under reduced pressure. The yield of crude 2,3-dihydro-2-methyl-1H-benz[e]inden-1-one was 23.4 g or 93%. Distillation of the crude product under reduced pressure (b.p. 130° C., 0.5 mbar) gave 18.7 g (75%) of 2,3-dihydro-2-methyl-1H-benz[e]inden-1-one, which crystallized upon standing at room temperature. During the addition (30 min) the temperature was kept at room temperature After the addition the organic layer was separated The organic layer was successively washed twice with a 5 wt % aqueous hydrochloric acid solution (150 ml) and once with a 2 wt % aqueous sodium bicarbonate solution (150 ml) After drying over anhydrous magnesium sulfate the solution was concentrated under reduced pressure Distillation of the crude product under reduced pressure (b.p. 130° C., 0.5 mbar)