Carbon Dioxide → HCID 16103488, compound

Participants

Reaction Conditions

Reaction Steps

Compound 68 (8.6 g, 0.016 mol), copper powder (0.7 g) and quinoline (50 mL) are 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 is cooled to room temperature and hexane (200 mL) is added. This mixture is washed repeatedly with HCl (1-2 M in water) to remove quinoline. The organic layer is dried over MgSO4 and concentrated by evaporation, and the residue is 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