HuagongsheHuagongshe Chemistry Print Report · For research reference only
Propargyl alcohol → 3-[3,5-Bis(trifluoromethyl)phenyl]prop-2-yn-1-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Propargyl alcohol | HCID 7859 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-Iodo-3,5-bis(trifluoromethyl)benzene | HCID 630970 | — |
| 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 | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | 3-[3,5-Bis(trifluoromethyl)phenyl]prop-2-yn-1-ol | HCID 2736179 | — |
Reaction Steps
A mixture of 1-iodo-3,5-bis(trifluoromethyl)benzene (5.00 g), copper(I) iodide (56.0 mg), triphenylphosphine (193 mg), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (304 mg), propargyl alcohol (0.954 ml), diisopropylethylamine (10.2 ml) and tetrahydrofuran (100 ml) was stirred at room temperature for 6 hr. The reaction mixture was added to brine, 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=99:1-80:20) to give the object product (3.81 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-f451523d54274437aba05b89767597f9 |
| Source note | uspto-grants-2012_03 |