HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 1-Indanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Allyl bromide | HCID 7841 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1H-Inden-1-one, 2,3-dihydro-2-hydroxy- | HCID 3014017 | — |
| Reactant | 2-Hydroxytetralin-1-one | HCID 11008236 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | 1-Indanone | HCID 6735 | — |
| Product | N,N-Diethylaniline | HCID 7061 | — |
Reaction Steps
A commercially available hydroxy-tetralone or hydroxyindanone is treated with an allyl bromide in the presence of a base such as Cs2CO3 in a solvent such as DMF to afford the ether. Claisen rearrangement in a solvent such as diethylaniline affords the substituted tetralone or indanone. The Mitsunobu reaction then affords the 2-imidazolyl-1-R3-ethoxy)prop-2-enyl compound. Alternatively, the substituted tetralone or indanone is reduced with a catalyst such as RhCl(PPh3)3 in the presence of H2 neat to afford a (prop-2-enyl)phenol derivative. Mitsunobu reaction of the phenol the desired imidazole alcohol affords the 2-imidazolyl-1-R3-ethoxy prop-2-enyl tetralone or indanone derivative.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06943183B2 |
| Source dataset | uspto-grants-2005_09 |
| ORD ID | ord-9e891cfdc18443b6a347177152bdea5b |
| Source note | uspto-grants-2005_09 |