Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Tetrahydro-2-(2-propynyloxy)-2H-pyran | HCID 98609 | — |
| Reactant | 4-Bromo-1-methoxy-2-methylbenzene | HCID 608315 | — |
| Reactant | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| Catalyst | Bis(acetonitrile)dichloropalladium | HCID 6093782 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | HCID 59407851 | HCID 59407851 | — |
Reaction Steps
A mixture of 4-bromo-2-methylanisole (3.02 g), cesium carbonate (12.7 g), 2-(2-propynyloxy)tetrahydropyran (3.16 ml), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (429 mg), bis(acetonitrile)palladium(II) dichloride (77.8 mg) and acetonitrile (100 ml) was stirred at 80° C. for 5 hr. The reaction mixture was added to brine, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0-90:10) to give the object product (1.76 g) as a pale-brown oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08129361B2 |
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| Source dataset | uspto-grants-2012_03 |
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| ORD ID | ord-2444411ee20843a59a360217eaba9d13 |
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| Source note | uspto-grants-2012_03 |
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