HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → Methyl 2-(hex-1-yn-1-yl)benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 1-Hexyne | HCID 12732 | — |
| Reactant | Benzoic acid, 2-iodo-, ion(1-) | HCID 4739928 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Product | Methyl 2-(hex-1-yn-1-yl)benzoate | HCID 11333401 | 90% |
Reaction Steps
Coupling of 2-iodobenzoate (3.0 g, 11.5 mmol) with 1-hexyne (2.71 mL, 22.9 mmol) using Pd(PPh3)2Cl2 and CuI in DMF at room temperature gave 2.23 g (90%) of compound 157 as a brown oil. 1H NMR (400 MHz, CDCl3): δ 0.95 (t, J=7.3 Hz, 3H), 1.45-1.55 (m, 2H), 1.55-1.65 (m, 2H), 2.47 (t, J=7.0 Hz, 2H), 3.91 (s, 3H), 7.26-7.33 (m, 1H), 7.37-7.44 (m, 1H), 7.50 (d, J=7.7 Hz, 1H), 7.87 (d, J=7.9 Hz, 1H). LCMS (APCI): m/z 217 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07649093B2 |
| Source dataset | uspto-grants-2010_01 |
| ORD ID | ord-fd38002cbe2b49cb9980a0817842f9d7 |
| Source note | uspto-grants-2010_01 |