HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzyl diethyl phosphate → 4-Benzyl-furan-2-carbaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzyl diethyl phosphate | HCID 298808 | — |
| Reactant | 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehyde | HCID 3547541 | — |
| Reactant | 5-Benzylfuran-2-carbaldehyde | HCID 12418537 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Acetonitrile 2-propanol | HCID 21921005 | — |
| Product | 4-Benzyl-furan-2-carbaldehyde | HCID 59648585 | 41% |
Reaction Steps
The title compound was synthesized from 5-formylfuran-3-boronic acid pinacol ester (878 mg, 3.95 mmol), and benzyl diethyl phosphate (1.25 g, 5.14 mmol) using the same conditions used to synthesize 5-benzyl-furan-2-carbaldehyde, with the exception that TPP and Pd(OAc)2 were dissolved in 2:1 CH3CN/isopropyl alcohol. Purification by flash chromatography yielded 4-benzyl-furan-2-carbaldehyde as a white solid (300 mg, 41%). 1H NMR (400 MHz, CDCl3) δ ppm 9.56 (s, 1 H) 7.29-7.38 (m, 3 H) 7.24-7.28 (m, 2 H) 7.17 (d, J=3.5 Hz, 1 H) 6.19 (d, J=3.6 Hz, 1 H) 4.07 (s, 2 H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07579370B2 |
| Source dataset | uspto-grants-2009_08 |
| ORD ID | ord-38e9e691354f4cd9a9ea970ac403aada |
| Source note | uspto-grants-2009_08 |