HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1734849Generated: October 28, 2026
Tetrahydrofuran → 1-(4-Methylphenylsulfonyl)-5-(1-dodecynyl)indole-3-carboxaldehyde
https://huagongshe.com/reaction/1734849
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | 1-Decyne | HCID 12997 | — |
| Reactant | 5-bromo-1-(4-methylbenzenesulfonyl)-1H-indole-3-carbaldehyde | HCID 10384969 | — |
| Catalyst | Copper iodide | HCID 83717 | — |
| Catalyst | Dichlorobis(triphenylphosphine)palladium | HCID 6102075 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 1-(4-Methylphenylsulfonyl)-5-(1-dodecynyl)indole-3-carboxaldehyde | HCID 18372939 | 50.8% |
Reaction Steps
To a degassed mixture of 1-(4-methylphenylsulfonyl)-5-bromoindole-3-carboxaldehyde (36.9 g), 1-decyne (16.8 g), in dry triethylamine (200 ml) and dry tetrahydrofuran (150 ml) was added, 1 mole percent of copper (II) iodide and 2 mole percent of bis(triphenylphosphine)palladium (II) chloride. The reaction mixture was stirred at 65° C. for 7 days. The solution was evaporated, and the residue was flash chromatographed (silica gel:4:1, dichloromethane:heptane). The appropriate fractions were collected and evaporated. The residue was recrystallized from hexane to give 23.1 g (50.8%) of product, mp 84°-86° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05534640 |
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| Source dataset | uspto-grants-1996_07 |
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| ORD ID | ord-19e2eca77a934b959011fc507b901595 |
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| Source note | uspto-grants-1996_07 |
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