6-Nitroindan-1-one → 6-Nitro-2,3-dihydro-1H-inden-1-ol

HRID 324985Notes

Reaction equation

HRID 324985 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][C:10]2=[O:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].[BH4-].[Na+]>CO>[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][CH:10]2[OH:13])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 905626-Nitroindan-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 143168096-Nitro-2,3-dihydro-1H-inden-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 6-nitro-1-indanone (18.9 g, 107 mmol) in methanol (300 mL) was cooled to 0° C. and sodium borohydride (4.04 g, 107 mmol) was added in several small portions. The reaction was then stirred overnight at 25° C. The solution was quenched at 0° C. with methanolic hydrochloric acid (200 mL), concentrated under reduced pressure, redissolved in dichloromethane, washed with water, and the organic layer reconcentrated to provide the crude alcohol as a brown solid which was used without further purification in Preparation 3.

Workup

  1. customThe solution was quenched at 0° C. with methanolic hydrochloric acid (200 mL)
  2. concentrationconcentrated under reduced pressure
  3. dissolutionredissolved in dichloromethane
  4. washwashed with water

Sources & evidence

ORD record
ord-d0f63315529e4e8ea971ff7d6b6b0179
Source dataset
uspto-grants-2001_04
Patent number
US06221876B1

Reaction notes

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