Water → 2-Hydroxy-5-nitroindane
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][C:8](=[O:13])[CH2:7]2)([O-:3])=[O:2].[BH4-].[Na+].O>CCO.CC(O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([OH:13])[CH2:7]2)([O-:3])=[O:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
5-nitro-2-indanone (5.3 g, 30 mmol) was dissolved in EtOH: i-PrOH (1:1, 150 mL). NaBH4 (1.7 g, 45 mmol) was added portion by portion at room temperature. The reaction mixture was stirred at r.t for additional 30 min and water was added at 0° C. (ice-water bath). The reaction mixture was extracted with EtOAc (100 mL×3) and the combined organic layers were washed with water and brine and dried over Na2SO4. Purification of the concentrated crude product by column chromatography (EtOAc:Hexane=4:6) afforded the title product as a pale yellow oil (4.47 g, 83%).