HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylborane → 2-(2-Fluoro-5-nitrophenyl)-2-methylpent-4-enal
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylborane | HCID 7357 | — |
| Reactant | Allyl Alcohol | HCID 7858 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Lithium Chloride | HCID 433294 | — |
| Reactant | 2-(2-Fluoro-5-nitrophenyl)propanal | HCID 86600438 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | 2-(2-Fluoro-5-nitrophenyl)-2-methylpent-4-enal | HCID 86600439 | — |
Reaction Steps
To a solution of palladium acetate (0.1 eq), triphenylphosphine (0.2 eq), lithium chloride (1.0 eq) in THF were sequentially added 2-(2-fluoro-5-nitrophenyl) propanal (1.1 eq) in THF, allyl alcohol (1.0 eq), triethylamine (1.2 eq) and triethylborane (2.4 eq) under nitrogen at room temperature. Solution was allowed to stir for 2 h. Mixture was diluted with saturated solution of sodium bicarbonate, extracted with ethyl acetate. Organics were washed with brine, dried with sodium sulfate and concentrated. Crude product was purified using flash chromatography (85% Hex:15% EtoAc) on silica to afford 2-(2-fluoro-5-nitrophenyl)-2-methylpent-4-enal.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08415382B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-70e4ac7b5f4c44abac87bf28a2206406 |
| Source note | uspto-grants-2013_04 |