Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Carbon Dioxide | HCID 280 | — |
| Reactant | Quinoline | HCID 7047 | — |
| Reactant | 3,5-Didecanyldithieno[3,2-b:2',3'-d]thiophene-2,6-dicarboxylic acid | HCID 16103457 | — |
| Catalyst | Copper | HCID 23978 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | HCID 16103488 | HCID 16103488 | 47.4% |
Reaction Steps
Compound 68 (8.6 g, 0.016 mol), copper powder (0.7 g) and quinoline (50 mL) were combined and heated at 250-260° C. in a Woods-metal bath. When no further bubbles of carbon dioxide gas could be detected (about 2 hours), the mixture was cooled to room temperature and hexane (200 mL) was added. This mixture was washed repeatedly with HCl (1-2 M in water) to remove quinoline. The organic layer was dried over MgSO4 and concentrated by evaporation, and the residue was purified by column chromatography (SiO2/hexanes) to yield compound 63 (3.4 g, 47.4%). 1H NMR (CD2Cl2) δ 6.97 (s, 2H), 2.73 (t, 4H), 1.78 (m, 4H), 1.27 (m, 28H), 0.88 (t, 6H). 13C NMR: 141.89, 136.75, 130.99, 120.57, 32.33, 30.02, 29.79 (m, overlap), 29.74, 29.15, 23.10, 14.28.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07705108B2 |
|---|
| Source dataset | uspto-grants-2010_04 |
|---|
| ORD ID | ord-a30762a7610d448b91ac73b073f7f522 |
|---|
| Source note | uspto-grants-2010_04 |
|---|
