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

HRID 1028466Notes

Reaction equation

HRID 1028466 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+]>CO.O1CCCC1>[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

5

Reactant 2

HCID 5206955-Bromo-1-indanoneHCID 4311764Sodium borohydride

Product 1

HCID 134862995-bromo-2,3-dihydro-1H-inden-1-olYield 100.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromoindanone (2.2 g, 0.01 mol) in a mixture of methanol (50 mL) and tetrahydrofuran (10 mL) was added sodium borohydride (0.78 g, 0.02 mol) and the reaction mixture was stirred at room temperature overnight. The solution was concentrated and the residue was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated to give 2.15 g of crude material. 1H NMR (300 MHz, CDCl3) 6 ppm 157 (s, 1 H) 1.87-2.02 (m, 1 H) 2.40-2.59 (m, 1 H) 2.73-2.88 (m, 1 H) 2.95-3.11 (m, 1 H) 5.12-5.25 (m, 1 H) 7.29 (s, 1 H) 7.32-7.43 (m, 2 H). MS (ESI), m/z 416.0 (M+205)+.

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was partitioned between water and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-4a7a2bb46c28405bbbb74c3b69e1e581
Source dataset
uspto-grants-2014_05
Patent number
US08735595B2

Reaction notes

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