Potassium Carbonate → 4'-Benzyloxyphenyl acetylene

HRID 2243567Notes

Reaction equation

HRID 2243567 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[C:22][Si](C)(C)C)=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CO>[CH2:7]([O:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]#[CH:22])=[CH:19][CH:20]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 58608141((4-(Benzyloxy)phenyl)ethynyl)trimethylsilane

Product 1

HCID 14903234'-Benzyloxyphenyl acetylene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (11.1 g, 80.5 mmol) was added to a solution of the (4-benzyloxy-phenylethynyl)trimethylsilane 101 (13, from above) in methanol (70 mL). The mixture stirred at room temperature for 16 h and was partitioned between ethyl acetate and water. The aqueous phase was separated and extracted with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated to afford a dark brown solid. This material was purified via column chromatography (eluting with 0-5% ethyl acetate-hexane) to afford 1-benzyloxy-4-ethynyl-benzene 102a as an off-white solid.

Workup

  1. customwas partitioned between ethyl acetate and water
  2. customThe aqueous phase was separated
  3. extractionextracted with ethyl acetate
  4. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a dark brown solid
  9. customThis material was purified via column chromatography (eluting with 0-5% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-4dc6f23f12ec479087ccfcc6ac4e962c
Source dataset
uspto-grants-2010_03
Patent number
US07674907B2

Reaction notes

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