Water → Methyl 2-((trimethylsilyl)ethynyl)benzoate

HRID 1802816

Reaction equation

HRID 1802816 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7](I)=[CH:6][CH:5]=1.[C:12]([Si:14]([CH3:17])([CH3:16])[CH3:15])#[CH:13].C(N(CC)CC)C.O>O1CCCC1.[Cu]I>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:13]#[C:12][Si:14]([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 69273Methyl 4-iodobenzoate

Product 1

HCID 11053512Methyl 2-((trimethylsilyl)ethynyl)benzoateYield 100.2%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

20.60 g (78.61 mmol) of 4-Iodobenzoic acid methyl ester and 9.26 g (94.33 mmol) of ethynyl trimethylsilane were dissolved in 200 ml of tetrahydrofuran, and thereto 23.86 g (235.83 mmol) of triethylamine, 1.65 g (2.36 mmol) of dichloro(bistriphenylphosphine)palladium(II) and 0.45 g (2.36 mmol) of copper(I) iodide were added. The mixture was stirred at room temperature for 8 hours. At the end of reaction, added water and extracted with ethylacetate. The extract was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and separated by column chromatography to obtain trimethylsilylethynylbenzoic acid methyl ester 18.30 g (Yield 100%).

Workup

  1. customAt the end of reaction
  2. extractionextracted with ethylacetate
  3. washThe extract was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customseparated by column chromatography

Sources & evidence

ORD record
ord-a38fee4a0dc94c7694a1e30f0d4038ba
Source dataset
uspto-grants-2013_01
Patent number
US08349885B2

Linked notes

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