5-Bromo-1-indanone → 5-bromo-2,3-dihydro-1H-inden-1-ol

HRID 2360048Notes

Reaction equation

HRID 2360048 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([OH:11])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 5206955-Bromo-1-indanoneHCID 4311764Sodium borohydride

Product 1

HCID 134862995-bromo-2,3-dihydro-1H-inden-1-olYield 145.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 5-bromo-2,3-dihydro-1H-inden-1-one (2.07 g, 9.81 mmol) in ethanol (49 mL) was treated with the sodium borohydride (186 mg, 4.90 mmol) all at once. After a few minutes, the solution warmed slightly and all solids dissolved. After stirring at room temperature for 1 h, the mixture was concentrated in vacuo to remove ethanol. The gum obtained was partitioned between ethyl acetate and water. The organic layer was extracted with saturated sodium bicarbonate solution (2×) and saturated sodium chloride solution. Drying (Na2SO4) and concentration in vacuo afforded the title compound (3.05 g, 98%) as a colorless oil, which crystallized upon pumping under high vacuum overnight.

Workup

  1. waitAfter a few minutes
  2. temperaturethe solution warmed slightly
  3. dissolutionall solids dissolved
  4. concentrationthe mixture was concentrated in vacuo
  5. customto remove ethanol
  6. customThe gum obtained
  7. customwas partitioned between ethyl acetate and water
  8. extractionThe organic layer was extracted with saturated sodium bicarbonate solution (2×) and saturated sodium chloride solution
  9. customDrying
  10. concentration(Na2SO4) and concentration in vacuo

Sources & evidence

ORD record
ord-9997e75060744eb69de7a6e9fb1ce2c0
Source dataset
uspto-grants-2014_04
Patent number
US08685991B2

Reaction notes

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