Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Triethylamine | HCID 8471 | — |
| Edukt | Trimethylsilylacetylene | HCID 66111 | — |
| Edukt | Benzoic acid, 2-iodo-, methyl ester | HCID 69132 | — |
| Katalysator | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | Methyl 2-((trimethylsilyl)ethynyl)benzoate | HCID 11053512 | 85,1% |
Reaktionsschritte
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.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patentnummer | US08106077B2 |
|---|
| Quelldatensatz | uspto-grants-2012_01 |
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| ORD ID | ord-b3cb5dace8cb4b3cb449666ab2002aaa |
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| Quellennotiz | uspto-grants-2012_01 |
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