HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → HCID 59497686, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 1-Naphthalenemethanol | HCID 20908 | — |
| Reactant | Diisopropyl diazene-1,2-dicarboxylate | HCID 75555 | — |
| Reactant | 1,3-Dihydro-1-(1-methylvinyl)-2H-benzimidazol-2-one | HCID 100278 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59497686 | HCID 59497686 | 89.3% |
Reaction Steps
To a solution of 1-isopropenylbenzimidazolone (1.0 g, 5.7 mmol) in dry THF (80 mL) are added triphenylphosphine (1.8 g, 6.9 mmol) and naphthalen-1-yl-methanol (1.1 g, 6.9 mmol). Then diisopropyl azodicarboxylate (1.4 mL, 6.9 mmol) is added drop wise into the above solution at room temperature. The mixture is stirred for 16 hrs and then the solvent is removed under vacuum. The residue is purified by flash column chromatography using 10% EtOAc in hexanes to give 1.6 g (89%) of 1-isopropenyl-3-naphthalen-1-ylmethyl-1,3-dihydro-benzimidazol-2-one.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09150556B2 |
| Source dataset | uspto-grants-2015_10 |
| ORD ID | ord-deddd4b417684acc9696749a9bb571b1 |
| Source note | uspto-grants-2015_10 |