HuagongsheHuagongshe Chemistry Print Report · For research reference only
Propargyl alcohol → 3-(2-Thienyl)-2-propyn-1-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Propargyl alcohol | HCID 7859 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 2-Iodothiophene | HCID 18921 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | 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 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-(2-Thienyl)-2-propyn-1-ol | HCID 11040769 | — |
Reaction Steps
A mixture of 2-iodothiophene(5.00 g), copper(I) iodide (91 mg), triphenylphosphine (315 mg), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (497 mg), propargyl alcohol (1.54 ml), diisopropylethylamine (16.6 ml) and tetrahydrofuran (50 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 (1.45 g) as a brown oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08129361B2 |
| Source dataset | uspto-grants-2012_03 |
| ORD ID | ord-b4e8221b0e264acea0be1fd76f80a1a4 |
| Source note | uspto-grants-2012_03 |