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

HRID 929466Notes

Reaction equation

HRID 929466 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 86667884(R)-1-(tert-butyldimethylsilyloxy)pent-4-yn-2-olYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (2.14 g, 15.5 mmol) was added to a solution of (R)-1-(tert-butyldimethylsilyloxy)-5-(trimethylsilyl)pent-4-yn-2-ol (3 g, 10.6 mmol) in methanol (100 mL) and the mixture stirred at room temperature for 8 hours. The solvent was removed under reduced pressure and aqueous ammonium chloride solution (100 mL) was added to the resulting oil. The mixture was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine, dried (MgSO4) and concentrated under reduced pressure. The crude material was purified by flash chromatography (biotage) using a gradient of EtOAc in hexane to afford (R)-1-(tert-butyldimethylsilyloxy)pent-4-yn-2-ol (1.81 g, 8.44 mmol, 80%).

Workup

  1. customThe solvent was removed under reduced pressure and aqueous ammonium chloride solution (100 mL)
  2. additionwas added to the resulting oil
  3. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by flash chromatography (biotage)

Sources & evidence

ORD record
ord-35a022026ab9477aba1718f0d268aa19
Source dataset
uspto-grants-2016_03
Patent number
US09296686B2

Reaction notes

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