Water → 2-Hydroxy-5-nitroindane

HRID 1881353Notes

Reaction equation

HRID 1881353 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

HCID 962WaterHCID 15020665-Nitro-2-indanoneHCID 4311764Sodium borohydride

Product 1

HCID 36859272-Hydroxy-5-nitroindaneYield 83.2%

Reagents, catalysts & solvents 1

HCID 22179027Isopropanol ethanolSolvent

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%).

Workup

  1. extractionThe reaction mixture was extracted with EtOAc (100 mL×3)
  2. washthe combined organic layers were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. customPurification of the
  5. concentrationconcentrated crude product by column chromatography (EtOAc:Hexane=4:6)

Sources & evidence

ORD record
ord-943281951add4b10a35157f9b1f2a570
Source dataset
uspto-grants-2012_11
Patent number
US08318790B2

Reaction notes

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