2,2-dimethyl-2,3-dihydro-1H-inden-1-one → 2,3-Dihydro-2,2-dimethyl-1H-inden-1-ol
Reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:11].[BH4-].[Na+]>CO>[CH3:1][C:2]1([CH3:12])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]1[OH:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2,2-dimethyl-indan-1-one, which can be prepared as described in Ranu, B. C.; Jana, U. Journal of Organic Chemistry, 1999, 64, 6380-6386, (13.0 g, 81.3 mmol) in methanol (200 mL) at −20° C. is added NaBH4 (3.07 g, 81.3 mmol). Upon complete consumption of the starting ketone, as determined by TLC analysis, the reaction is quenched with saturated aqueous NH4Cl. The reaction mixture is then concentrated to near dryness, diluted with ethyl acetate and washed with water. The organic layer is then dried with Na2SO4, filtered, and concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:8) to provide 2,2-dimethyl-indan-1-ol. 1H NMR (400 MHz, CDCl3) δ ppm 1δ ppm 1.05 (s, 3 H), 1.20 (s, 3 H), 2.56-2.89 (m, 2 H), 4.70 (s, 1 H), 7.16-7.26 (m, 3 H), 7.35-7.42 (m, 1 H).