HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cyclopropylacetylene → HCID 68539387, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cyclopropylacetylene | HCID 138823 | — |
| Reactant | Methyl 4-methoxy-2-(trifluoromethylsulfonyloxy)benzoate | HCID 10710352 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 68539387 | HCID 68539387 | 96% |
Reaction Steps
Coupling of methyl 4-(methyloxy)-2-{[(trifluoromethyl)sulfonyl]oxy}benzoate (77) (0.70 g, 2.23 mmol) with cyclopropyl acetylene (0.30 g, 4.46 mmol) using Pd(PPh3)2Cl2 and CuI in DMF at room temperature gave 0.49 g (96%) of the title compound (149) as a brown oil. 1H NMR (400 MHz, CDCl3): δ 0.80-0.95 (m, 4H), 1.45-1.55 (m, 1H), 3.82 (s, 3H), 3.87 (s, 3H), 6.80 (dd, J1=8.9 Hz, J2=2.7 Hz, 1H), 6.96 (d, J=2.8 Hz, 1H), 7.88 (d, J=8.8 Hz, 1H). LCMS (ESI): m/z 231 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07649093B2 |
| Source dataset | uspto-grants-2010_01 |
| ORD ID | ord-7c56a57fb0214d09888f563ab11f1227 |
| Source note | uspto-grants-2010_01 |