Potassium Carbonate → HCID 21830640, compound

HRID 1600940Notes

Reaction equation

HRID 1600940 reaction equation
C(=O)([O-])[O-].[K+].[K+].[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH2:14][CH:15]([OH:22])[C:16]#[C:17][Si](C)(C)C)[CH:8]=1>CO>[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH2:14][CH:15]([OH:22])[C:16]#[CH:17])[CH:8]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 21830664HCID 21830664, compound

Product 1

HCID 21830640HCID 21830640, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Solid potassium carbonate (1.5 g) was added to a solution of (±)-5-(3-pyridyl)-1-(trimethylsilyl)pent-1-yn-3-ol (2.9 g) in methanol (50 ml) and the mixture stirred at room temperature for 24 hours. The methanol was removed under reduced pressure and water was added. The mixture was extracted with dichloromethane, the extracts dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with ethyl acetate to give the sub-title compound as an oil (1.8 g) which was used immediately.

Workup

  1. customThe methanol was removed under reduced pressure and water
  2. additionwas added
  3. extractionThe mixture was extracted with dichloromethane
  4. dry with materialthe extracts dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography over silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-bf386508aebf4ae38dfd9c58b064ee97
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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