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

HRID 1742410Notes

Reaction equation

HRID 1742410 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7]2>CO>[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH:9]([OH:13])[CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 5206955-Bromo-1-indanoneHCID 4311764Sodium borohydride

Product 1

HCID 134862995-bromo-2,3-dihydro-1H-inden-1-olYield 100.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.891 grams, 23.45 mmol) was added to a mixture of 5-bromo-indan-1-one (2.0g, 9.38 mmol)in MeOH (25 mL) at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred for 3 hours and quenched with saturated aqueous NH4Cl (25 mL) was added. The reaction mixture was diluted with EtOAc (200 mL). The organic layer was separated and was washed with saturated aqueous NaCl (3×50 mL), dried over sodium sulfate (Na2SO4) and concentrated in vacuo to yield 2.0 grams of a brown oil. 1H NMR (250 MHz, CDCl3): d 7.26 (m, 3 H), 5.18 (t, 1 H), 3.03 (m, 1 H), 2.80 (m, 1 H), 2.50 (m, 1 H), 193 (m, 1 H).

Workup

  1. customquenched with saturated aqueous NH4Cl (25 mL)
  2. additionwas added
  3. additionThe reaction mixture was diluted with EtOAc (200 mL)
  4. customThe organic layer was separated
  5. washwas washed with saturated aqueous NaCl (3×50 mL)
  6. dry with materialdried over sodium sulfate (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-03ff7f0e40c049bab2a22955061ec73a
Source dataset
uspto-grants-1994_08
Patent number
US05338740

Reaction notes

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