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

HRID 731175Notes

Reaction equation

HRID 731175 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>[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-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a clear solution of 5-bromo-1-indanone (1.0 g, 4.7 mmol) in MeOH (6 mL) was added NaBH4 (0.36 g, 9.5 mmol). The mixture was stirred at room temperature overnight. The mixture was concentrated to dryness and redissolved in water/EtOAc. The layers were separated and the EtOAc layer was dried with anhydrous Na2SO4 and concentrated to obtain 1.1, which was used directly in the next step. 1HNMR (DMSO-d6) δ 7.41 (s, 1H), 7.36 (d, 1H, J2=8.08 Hz), 7.26 (d, 1H, J1=7.99 Hz), 5.28 (d, 1H, J=5.90 Hz), 4.99 (q, 1H), 2.91 (m, 1H), 2.71 (m, 1H), 2.33 (m, 1H), 1.78 (m, 1H).

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. dissolutionredissolved in water/EtOAc
  3. customThe layers were separated
  4. dry with materialthe EtOAc layer was dried with anhydrous Na2SO4
  5. concentrationconcentrated
  6. customto obtain 1.1, which

Sources & evidence

ORD record
ord-768e892ba5e040f1a3d1e96fed6dd3b4
Source dataset
uspto-grants-2009_09
Patent number
US07582803B2

Reaction notes

Loading…