HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Propargyl alcohol → 3-(5-Methyl-2-thienyl)-2-propyne-1-ol
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Propargyl alcohol | HCID 7859 | — |
| Edukt | Triphenylphosphine | HCID 11776 | — |
| Edukt | Diisopropylethylamine | HCID 81531 | — |
| Edukt | 2-Iodo-5-methylthiophene | HCID 140096 | — |
| Katalysator | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Katalysator | Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1) | HCID 11029508 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Lösungsmittel | Tetrahydrofuran | HCID 8028 | — |
| Produkt | 3-(5-Methyl-2-thienyl)-2-propyne-1-ol | HCID 59407516 | — |
Reaktionsschritte
A mixture of 2-iodo-5-methylthiophene (5.00 g), copper(I) iodide (82 mg), triphenylphosphine (286 mg), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (445 mg), propargyl alcohol (1.91 ml), diisopropylethylamine (15.1 ml) and tetrahydrofuran (30 ml) was stirred at room temperature for 20 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1-2:1) to give the object product (1.48 g) as a brown oil.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08129361B2 |
| Quelldatensatz | uspto-grants-2012_03 |
| ORD ID | ord-39f77001690a4a04b01060a72968ea12 |
| Quellennotiz | uspto-grants-2012_03 |