2-methyl-2,3-dihydro-1H-cyclopenta[a]naphthalen-1-ol

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

Procedure: A mixture of 2-methyl-2,3-dihydro-1H-cyclopenta[a]naphthalen-1-ol (obtained as described above) and 1 g of p-toluenesulphonic acid in 200 mL of benzene was refluxed for 1 h. Then the reaction mixture was cooled to room temperature and treated with a saturated aqueous solution of Na2CO3. The organic phase was isolated, dried over MgSO4 and evaporated off to dryness. Yield 14.2 g (55% based on starting 2-methyl-2,3-dihydro-1H-cyclopenta[a]naphtalen-1-one). was refluxed for 1 h The organic phase was isolated dried over MgSO4 evaporated off to dryness

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

Procedure: 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

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

Procedure: 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

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

Procedure: 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