HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Heptyne → Methyl 2-(1-heptyn-1-yl)-4-(methyloxy)benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Heptyne | HCID 12350 | — |
| 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 | — |
| Product | Methyl 2-(1-heptyn-1-yl)-4-(methyloxy)benzoate | HCID 68536171 | 100.9% |
Reaction Steps
Coupling of methyl 4-(methyloxy)-2-{[(trifluoromethyl)sulfonyl]oxy}benzoate (77) (0.80 g, 2.55 mmol) with 1-heptyne (0.70 mL, 5.10 mmol) using Pd(PPh3)2Cl2 and CuI gave 0.67 g (˜100%) of compound 110 as a brown oil. 1H NMR (400 MHz, CDCl3): δ 0.92 (t, J=7.3 Hz, 3H), 1.30-1.50 (m, 4H), 1.60-1.70 (m, 2H), 2.47 (t, J=7.2 Hz, 2H), 3.83 (s, 3H), 3.87 (s, 3H), 6.82 (dd, J1=8.9 Hz, J2=2.7 Hz, 1H), 6.99 (d, J=2.7 Hz, 1H), 7.89 (d, J=8.8 Hz, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07649093B2 |
| Source dataset | uspto-grants-2010_01 |
| ORD ID | ord-e1884d3105b641558728dddf25c62e58 |
| Source note | uspto-grants-2010_01 |