4-Nitroindan-1-one → 4-Nitro-2,3-dihydro-1H-inden-1-OL

HRID 241797

Reaction equation

HRID 241797 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][C:8]2=[O:13])([O-:3])=[O:2].[BH4-].[Na+]>CO>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][CH:8]2[OH:13])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 905634-Nitroindan-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 131024564-Nitro-2,3-dihydro-1H-inden-1-OL

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 4-nitro-2,3-dihydro-1H-inden-1-one (149 mgs, 0.84 mmol, 1.0 equiv) in MeOH (2 mL) was added NaBH4 (10 mg, 0.26 mmol, 0.33 equiv) as a solid in one portion. After stirring for 1 h at 0° C., the solvent was removed in vacuo, and water (3 mL) was added to the residue. The aqueous suspension was extracted three times with EtOAc, and the combined organic layers were dried over sodium sulfate. The solution was filtered and concentrated in vacuo. The desired product was used without further purification (135 mg, 90%).

Workup

  1. customthe solvent was removed in vacuo, and water (3 mL)
  2. additionwas added to the residue
  3. extractionThe aqueous suspension was extracted three times with EtOAc
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo
  7. customThe desired product was used without further purification (135 mg, 90%)

Sources & evidence

ORD record
ord-40c65f2bfd8e48e4930dc96c60de74c6
Source dataset
uspto-grants-2014_02
Patent number
US08653081B2

Linked notes

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