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

HRID 433326Notes

Reaction equation

HRID 433326 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 are suspended in 10 ml of ethanol and placed in an ultrasonic bath for 4 h. The reaction mixture is then acidified with 2N HCl and stirred. The ethanol is distilled off, water and dichloromethane are added to the residue and the mixture is extracted with dichloromethane. The organic phase is separated off, dried over MgSO4, filtered and concentrated and the residue is purified chromatographically on silica gel using dichloromethane/methanol 20/1. This gives 5-chloro-2-methylsulfonylindan-1-ol of melting point 163° C.

Workup

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

Sources & evidence

ORD record
ord-314cccc883d54964b8a42ceec1782929
Source dataset
uspto-grants-2003_12
Patent number
US06667345B2

Reaction notes

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