HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,8-Diazabicyclo(5.4.0)undec-7-ene → 4(R)-Azido-6,8-dibromo-chroman
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | P,P-Diphenylphosphinic azide | HCID 199401 | — |
| Reactant | (S)-6,8-Dibromochroman-4-ol | HCID 67304261 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4(R)-Azido-6,8-dibromo-chroman | HCID 86620016 | — |
Reaction Steps
A solution containing 6,8-dibromo-chroman-4(S)-ol in tetrahydrofuran (0.17M) and 1.2 equivalents of diphenylphosphorylazide was stirred for 15 minutes at room temperature. The solution was cooled to 10° C. and 2.5 equivalents of 1,8-diazabicyclo[5.4.0]undec-7-ene added. The mixture was stirred with gradual warming to room temperature and maintained for 48 h. The mixture was diluted with ethylacetate and washed with brine followed by water. The organic phase was concentrated to afford the title compound as a tan oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07973050B2 |
| Source dataset | uspto-grants-2011_07 |
| ORD ID | ord-a7dbc9ef49184c28889d6fa51a957303 |
| Source note | uspto-grants-2011_07 |