HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 57704605, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1-Dimethylethyl N-(5-ethynyl-2,2-dimethyl-1,3-dioxan-5-yl)carbamate | HCID 11514385 | — |
| Reactant | HCID 57704617 | HCID 57704617 | — |
| Catalyst | Bis(acetonitrile)dichloropalladium | HCID 6093782 | — |
| Catalyst | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 57704605 | HCID 57704605 | 79.2% |
Reaction Steps
Compound 51-2 (9.48 g), (5-ethynyl-2,2-dimethyl-1,3-dioxan-5-yl)carbamic acid t-butyl ester (7.34 g) synthesized according to the known method (e.g., Tetrahedron vol. 57 (2001) 15 pages 6531-6538), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (868 mg), bis(acetonitrile)palladium(II) dichloride (157 mg) and cesium carbonate (25.6 g) were stirred in acetonitrile (200 ml) at 80° C. for 8 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the object product (11.1 g) as a pale-brown oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08129361B2 |
| Source dataset | uspto-grants-2012_03 |
| ORD ID | ord-7c2a512a64ae4ce298f24acbc21766c3 |
| Source note | uspto-grants-2012_03 |