Potassium Carbonate → (S)-1-(tert-butyldimethylsilyloxy)pent-4-yn-2-ol

HRID 335632Notes

Reaction equation

HRID 335632 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Si:7]([O:14][CH2:15][C@H:16]([OH:24])[CH2:17][C:18]#[C:19][Si](C)(C)C)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]>CO>[Si:7]([O:14][CH2:15][C@@H:16]([OH:24])[CH2:17][C:18]#[CH:19])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 53308767(R)-1-((tert-Butyldimethylsilyl)oxy)-5-(trimethylsilyl)pent-4-yn-2-ol

Product 1

HCID 86667887(S)-1-(tert-butyldimethylsilyloxy)pent-4-yn-2-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (1.5 eq) is added to a solution of (R)-1-(tert-butyldimethylsilyloxy)-5-(trimethylsilyl)pent-4-yn-2-ol (1 eq) in methanol and the mixture stirred at room temperature for 8 hours. The solvent is removed under reduced pressure and aqueous ammonium chloride solution added. The mixture is extracted with ethyl acetate (3×) and the combined organic layers washed with brine, dried (MgSO4), concentrated under reduced pressure and purified by flash chromatography (biotage) using a gradient of EtOAc in hexane.

Workup

  1. customThe solvent is removed under reduced pressure and aqueous ammonium chloride solution
  2. additionadded
  3. extractionThe mixture is extracted with ethyl acetate (3×)
  4. washthe combined organic layers washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. custompurified by flash chromatography (biotage)

Sources & evidence

ORD record
ord-59daf30586794fe1ac931dd4ff48647c
Source dataset
uspto-grants-2014_11
Patent number
US08884058B2

Reaction notes

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