HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 5-Cyclopropylethynyl-3-nitrothiophene-2-carboxylic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Cyclopropylacetylene | HCID 138823 | — |
| Reactant | Methyl 5-bromo-3-nitrothiophene-2-carboxylate | HCID 57618723 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 5-Cyclopropylethynyl-3-nitrothiophene-2-carboxylic acid methyl ester | HCID 68942096 | — |
Reaction Steps
Firstly bis(triphenylphosphine)palladium(II) chloride (17.6 mg) and then copper(I) iodide (19 mg) were added to a mixture of 5-bromo-3-nitrothiophene-2-carboxylic acid methyl ester (133 mg), ethynylcyclopropane (66 mg), triethylamine (51 mg), triphenylphosphine (3.3 mg) and THF (14 mL). After one hour, the reaction mixture was partitioned between water and ethyl acetate. The organic phase was dried over sodium sulfate and concentrated. The crude product was purified by preparative HPLC. The product with the molecular weight of 251.26 (C11H9NO4S) was obtained in this way; MS (ESI): 252 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08853208B2 |
| Source dataset | uspto-grants-2014_10 |
| ORD ID | ord-fc24ce8e6f1a43429493687898fce774 |
| Source note | uspto-grants-2014_10 |