Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 3-Methylbut-1-yne | HCID 69019 | — |
| Reactant | HCID 86762124 | HCID 86762124 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 56646065 | HCID 56646065 | 33.1% |
Reaction Steps
A mixture of Compound 19a (50 mg, 0.141 mmol), 3-methyl-1-butyne (48 mg, 0.705 mmol), sodium carbonate (74.6 mg, 0.704 mmol) and Cu (44.8 mg, 0.705 mmol) was heated in a sealed vessel at 120° C. for 32 h, adding every 8 h additional equal amounts of amounts of 3-methyl-1-butyne, sodium carbonate and Cu. Afterwards, the mixture was cooled, added with CH2Cl2, filtered on celite and evaporated to dryness in vacuo. The residue was purified by automated flash chromatography (SP1®TM-Biotage; gradient Petroleum Ether-EtOAc from 95:5 to 75:25 then isocratic Petroleum Ether-EtOAc from 9:1 giving 16 mg of the title product. Yield: 33.1%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08580962B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-ff2f3577a1d64a34bdaddf7611b565a4 |
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| Source note | uspto-grants-2013_11 |
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