Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Trifluoromethanesulfonate | HCID 2758875 | — |
| Reactant | HCID 178419772 | HCID 178419772 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Catalyst | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | HCID 6505921 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 18452898 | HCID 18452898 | 65% |
Reaction Steps
To a room temperature solution of 1.5 g (5.57 mmol) of the triflate from Step A above, 0.32 g (6.56 mmol) of bis(dibenzylideneacetone)palladium and 1,1′-bis(diphenylphosphino)-ferrocene in 15 mL of tetrahydrofuran is added to 12.25 mL (6.13 mmol) of a 0.5 M solution of benzylzinc bromide in tetrahydrofuran via syringe. The mixture is heated to 65° C. for 16 hr and cooled to room temperature. The mixture is poured into saturated ammonium chloride and extracted two times with ethyl acetate. The combined organic portions are dried (MgSO4), filtered, and concentrated in vacuo. Chromatography (Biotage, 100% toluene) of the residue affords 0.76 g (65%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07601738B2 |
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| Source dataset | uspto-grants-2009_10 |
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| ORD ID | ord-98fd2eda4dd44cd498793971e07cb94a |
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| Source note | uspto-grants-2009_10 |
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