反应详情

To a solution of 2,2-dimethyl-indan-1,3-dione (430 mg, 2.47 mmol), in ethanol (80 mL) at −30° C. is added a solution of NaBH4 (29 mg, 0.74 mmol) in ethanol (3 mL). After one h 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 twice 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)+.

1. customAfter one h the reaction is quenched with saturated aqueous NH4Cl
2. customis brought to room temperature
3. concentrationThe reaction mixture is concentrated to approximately half of its original volume
4. additiondiluted with ethyl acetate
5. washwashed with water
6. extractionThe aqueous layer is then back-extracted twice with ethyl acetate
7. dry with materialdried with Na2SO4
8. filtrationfiltered
9. concentrationconcentrated
10. customThe resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:6)