[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[C:5]([CH3:12])[CH:6]=[CH:7][C:8]=2[CH3:11])[C:3]1=[O:13].[BH4-].[Na+].CC(C)=O.[BH4-]>CCO>[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[C:5]([CH3:12])[CH:6]=[CH:7][C:8]=2[CH3:11])[CH:3]1[OH:13]8.95 g of 2,4,7-trimethylindanone (51.4 mmol) were dissolved in 70 ml of EtOH; the solution was cooled to 0° C. and 2.00 g of NaBH4 (51.8 mmol) were added to it in small aliquots. At the end of the addition, the reaction mixture was allowed to reach ambient temperature and then heated at 50° C. for 3 hours and 30 min. The reaction mixture was cooled to 0° C., and 50 ml of acetone were slowly (careful: exothermic reaction!) added to it to deactivate the residual borohydride. All volatiles were then removed in vacuo, the white solid obtained was treated with 50 ml of 1H2O and stirred for 30 min. The organic layer was extracted with Et2O (2×100 ml), washed with H2O, dried and essiccated in vacuo to leave 9.06 g of a white solid (100%).
Loading…
