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

HRID 731180Notes

Reaction equation

HRID 731180 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+]>CCO>[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 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-bromo-2,3-dihydroinden-1-one (47.1) (23.7 mmol) and NaBH4 (47.4 mmol) in EtOH (50 mL) was stirred at 60° C. for 6 minutes. After evaporation of the solvent, the residue was purified by chromatography (silica gel; 1:2 EtOAc/hexane) providing compound 47.2 in 100% yield. MS ESI (pos.) M/E: 195.0, 197.1 (M+H—H2O).

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was purified by chromatography (silica gel; 1:2 EtOAc/hexane)

Sources & evidence

ORD record
ord-714e10b9c59549809710b9f05efa3b7c
Source dataset
uspto-grants-2009_09
Patent number
US07582803B2

Reaction notes

Loading…