Sodium borohydride → 3,3-Difluoro-2,2-dimethylindan-1-ol
Reaction equation
[F:1][C:2]1([F:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[C:3]1([CH3:13])[CH3:12].[BH4-].[Na+]>C(O)C>[F:1][C:2]1([F:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([OH:11])[C:3]1([CH3:12])[CH3:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3,3-difluoro-2,2-dimethyl-indan-1-one (520 mg, 2.65 mmol) in ethanol (15 mL) is added NaBH4 (100 mg, 2.65 mmol). After 15 minutes the reaction is quenched with saturated aqueous NH4Cl and concentrated to near dryness. The resulting residue is diluted with ethyl acetate and washed with brine, dried with Na2SO4, filtered, and concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:6) to provide 3,3-difluoro-2,2-dimethyl-indan-1-ol; 1H NMR (400 MHz, CDCl3) δ ppm 1.07 (d, J=2.3 Hz, 2 H), 1.27 (d, J=2.3 Hz, 2 H), 4.79-4.83 (m, 1 H), 7.41-7.46 (m, 1 H), 7.48-7.60 (m, 3 H).