Water → HCID 57424260, compound

HRID 2377464Notes

Reaction equation

HRID 2377464 reaction equation
[CH:1]([O:4][C:5](=[O:18])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]#[C:13][Si](C)(C)C)[CH:7]=1)([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[CH:1]([O:4][C:5](=[O:18])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]#[CH:13])[CH:7]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 574242591-Methylethyl 3-[2-(trimethylsilyl)ethynyl]benzoate2×

Product 1

HCID 57424260HCID 57424260, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-trimethylsilanylethynyl-benzoic acid isopropyl ester (Intermediate 136, 0.6 g, 2.3 mmol) in anhydrous tetrahydrofuran (3 mL) was treated with a 1M solution of tetra-n-butyl ammonium fluoride in tetrahydrofuran (4.6 mL, 4.6 mmol) and the resulting reaction mixture was stirred in an ice bath for 5 min. Water was added and the reaction mixture was extracted with ethyl acetate. The organic phase was washed with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated to an oil that was purified by flash column chromatography using 5%-30% ethyl acetate in hexane as the eluent to afford the title compound as a solid (0.33 g, 76%).

Workup

  1. customthe resulting reaction mixture
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated to an oil that
  7. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-196334df84e74598b92f73c998627256
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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