Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2-Bromoanisole | HCID 11358 | — |
| Reactant | 1,4-Dioxa-8-azaspiro(4.5)decane | HCID 67435 | — |
| Reactant | Tri-o-tolylphosphine | HCID 80271 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | HCID 18727003 | HCID 18727003 | — |
Reaction Steps
A solution of 2-bromoanisole (6.00 g, 32.08 mmol) and 4-piperidone ethylene ketal (5.54 g, 38.69 mmol) in toluene (250 mL) was treated with sodium tert-butoxide (4.40 g, 45.76 mmol), tri-o-tolylphosphine (411 mg, 1.35 mmol), and tris(dibenzylideneacetone)dipalladium(0) (295 mg, 0.32 mmol) at room temperature. The mixture was heated in an oil bath (100° C., 2 h). The mixture was diluted with ether and the organics washed with brine, dried over Na2SO4, and concentrated under reduced pressure. Flash chromatography on silica gel (20% ethyl acetate/hexane) afforded the title compound (19).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06376503B1 |
|---|
| Source dataset | uspto-grants-2002_04 |
|---|
| ORD ID | ord-b3dc28f120744478b3d8feae4172b78e |
|---|
| Source note | uspto-grants-2002_04 |
|---|
