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

HRID 424795

Reaction equation

HRID 424795 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1I.[CH3:12][Si:13]([C:16]#[CH:17])([CH3:15])[CH3:14].C(N(CC)CC)C>CN(C=O)C.[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:17]#[C:16][Si:13]([CH3:15])([CH3:14])[CH3:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 69132Benzoic acid, 2-iodo-, methyl ester

Product 1

HCID 11053512Methyl 2-((trimethylsilyl)ethynyl)benzoateYield 85.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-iodo-benzoic acid methyl ester (792 mg, 3.02 mmol) in DMF (10 mL) are added trimethylsilylacetylene (854 μL, 6.04 mmol) and triethylamine (2.95 mL, 21.1 mmol). The reaction mixture is degassed for 20 minutes with a stream of nitrogen. Dichloro(bistriphenylphosphene) palladium (II) (212 mg, 0.302 mmol, 10 mol %) and copper (I) iodide (58 mg, 0.302 mmol, 10 mol %) are added and the reaction is heated to 80° C. After 3 h, the reaction is concentrated and the residue is chromatographed eluting with 0 to 5% EtOAc/Hexanes to yield the title compound (597 mg, 85%). GC/MS: 232.

Workup

  1. customThe reaction mixture is degassed for 20 minutes with a stream of nitrogen
  2. concentrationthe reaction is concentrated
  3. customthe residue is chromatographed
  4. washeluting with 0 to 5% EtOAc/Hexanes

Sources & evidence

ORD record
ord-b3cb5dace8cb4b3cb449666ab2002aaa
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Linked notes

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