[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[CH2:12][CH2:13][CH3:14])=[CH:5][CH:4]=1.[O-:15][Mn](=O)(=O)=O.[K+]>C(Cl)Cl.[O-]S([O-])(=O)=O.[Cu+2]>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6](=[CH:5][CH:4]=1)[C:7](=[O:15])[CH2:8][CH:9]2[CH2:12][CH2:13][CH3:14]The mixture of indans from step 2 (1.287 g, approx. 6.1 mmol) in CH2Cl2 (50 mL) was treated with a finely ground mixture of KMnO4 (7.00 g) and CuSO4.xH2O. The resulting mixture was heated at reflux for 89 hours, then cooled to room temperature and filtered through a celite pad. The filtrate was dried over MgSO4, filtered and evaporated under vacuum to an oil (1.155 g). The crude product was purified by chromatography on a Biotage FLASH 12M column, eluting with 10% EtOAc in hexanes, to afford 5-methoxy-3-propyl-1-indanone (0.188 g) as an oil. Other column fractions afforded 6-methoxy-3-propyl-1-indanone, the indan starting materials, and 5-methoxy-1-indanone.
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