2,2-Dimethyl-1H-indene-1,3(2H)-dione → 3-Hydroxy-2,2-dimethyl-1-indanone

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Reaction Steps

To a solution of 2,2-dimethyl-indan-1,3-dione (430 mg, 2.47 mmol), which can be prepared as described in Example 18, in ethanol (80 mL) at −30° C. is added a solution of NaBH4 (29 mg, 0.74 mmol) in ethanol (3 mL). After one hour the reaction is quenched with saturated aqueous NH4Cl and the mixture is brought to room temperature. The reaction mixture is concentrated to approximately half of its original volume and then diluted with ethyl acetate and washed with water. The aqueous layer is then back-extracted two times with ethyl acetate. The organic layers are combined, 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 afford 3-hydroxy-2,2-dimethyl-indan-1-one; MS: (ESI) m/z 177.0 (M+H)+.

Provenance & Evidence