[CH3:1][CH:2]1[C:14](=[O:15])[C:5]2=[C:6]3[C:11](=[CH:12][CH:13]=[C:4]2[CH2:3]1)[CH:10]=[CH:9][CH:8]=[CH:7]3.[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl>C1COCC1.CCOCC>[CH3:1][CH:2]1[CH:14]([OH:15])[C:5]2=[C:6]3[C:11](=[CH:12][CH:13]=[C:4]2[CH2:3]1)[CH:10]=[CH:9][CH:8]=[CH:7]3A 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.
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