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

HRID 2237417Notes

Reaction equation

HRID 2237417 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-935705a56c0846d2a3c3d411ec37f110
Source dataset
uspto-grants-2010_05
Patent number
US07718657B2

Reaction notes

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