3-Phenylthiopropan-2-one → 1-(Phenylthio)-2-propanol

HRID 1925533Notes

Reaction equation

HRID 1925533 reaction equation
[BH4-].[Na+].[C:3]1([S:9][CH2:10][C:11](=[O:13])[CH3:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO>[C:3]1([S:9][CH2:10][CH:11]([OH:13])[CH3:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 2471293-Phenylthiopropan-2-oneHCID 4311764Sodium borohydride

Product 1

HCID 997881-(Phenylthio)-2-propanolYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

732 mg (19.2 mmol) of NaBH4 were added in portions, while cooling (ice bath), to a solution of 2.46 g (14.8 mmol) of 1-(phenylthio)propan-2-one in methanol (18 ml). Stirring was then carried out for a further 2 h while cooling (ice bath). The mixture was then quenched with AcOH (17 ml) and then concentrated in vacuo. The residue was taken up in an ether/water mixture and neutralized with NaHCO3. The phases were separated and the organic phase was dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by means of CC (EA/hex 15:85), yielding 1.3 g (7.7 mmol, 52%) of 1-(phenylthio)propan-2-ol.

Workup

  1. temperaturewhile cooling (ice bath)
  2. temperaturewhile cooling (ice bath)
  3. customThe mixture was then quenched with AcOH (17 ml)
  4. concentrationconcentrated in vacuo
  5. customThe phases were separated
  6. dry with materialthe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by means of CC (EA/hex 15:85)

Sources & evidence

ORD record
ord-57ca5c735d4144818424ab4cca1f12d0
Source dataset
uspto-grants-2012_05
Patent number
US08178684B2

Reaction notes

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