HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 977561Generated: October 30, 2026
Tetrahydrofuran → 1-(4-Methylphenylsulfonyl)-5-(1-dodecynyl)indole-3-carboxaldehyde
https://huagongshe.com/reaction/977561
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 (11) 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:l, 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 |
|---|
| Patent number | US05614631 |
|---|
| Source dataset | uspto-grants-1997_03 |
|---|
| ORD ID | ord-1035e3f4295640ee8f6850fd4c5d71ed |
|---|
| Source note | uspto-grants-1997_03 |
|---|
