Hydrochloric Acid → 5-Chloro-2-methylsulfonylindan-1-ol

HRID 431301Notes

Reaction equation

HRID 431301 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH:6]([S:12]([CH3:15])(=[O:14])=[O:13])[CH2:5]2.[BH4-].[Na+].Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([OH:11])[CH:6]([S:12]([CH3:15])(=[O:14])=[O:13])[CH2:5]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 99648205-Chloro-2-methylsulfonylindan-1-one

Product 1

HCID 98347545-Chloro-2-methylsulfonylindan-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.489 g (2 mmol) of 5-chloro-2-methylsulfonylindan-1-one and 0.095 g (2.5 mmol) of sodium borohydride were suspended in 10 ml of ethanol and placed in an ultrasonic bath for 4 h. The reaction mixture was then acidified with 2N HCl and stirred. The ethanol was distilled off, water and dichloromethane were added to the residue and the mixture was extracted with dichloromethane. The organic phase was separated off, dried over MgSO4, filtered and concentrated and the residue was purified chromatographically on silica gel using dichloromethane/methanol 20/1. This gave 5-chloro-2-methylsulfonylindan-1-ol of melting point 163° C.

Workup

  1. distillationThe ethanol was distilled off
  2. additionwater and dichloromethane were added to the residue
  3. extractionthe mixture was extracted with dichloromethane
  4. customThe organic phase was separated off
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe residue was purified chromatographically on silica gel

Sources & evidence

ORD record
ord-1f8ec30a2c7f42bc9b66f70f68cca59f
Source dataset
uspto-grants-2003_12
Patent number
US06657086B2

Reaction notes

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