Carbon Dioxide → 3-Hexylthieno[3,2-b]thiophene

Participants

Reaction Conditions

Reaction Steps

A mixture of compound 62 (14.6 g, 0.054 mol), copper powder (2.00 g), and quinoline (80 mL) is heated at about 260° C. in a Woods metal bath. When no further bubbles of CO2 are detected (about 2 hours), the mixture is allowed to cool to room temperature, and hexane (200 mL) is added. The mixture is washed repeatedly with HCL (1-2 M in water) to remove the quinoline. The organic layer is dried over MgSO4 and concentrated by evaporation. The residue is purified by column chromatography (SiO2/hexanes) to yield compound 58 (25.1 g, 90.3% yield). GC/MS: 224 g/mol (M). 1H NMR (CD2Cl2): δ 7.36 (m, 1H), 7.25 (m, 1H), 7.01 (m, 1H), 2.73 (t, 2H), 1.69 (m, 2H), 1.34 (m, 6H), 0.89 (t, 3H). 13C NMR: 140.39, 139.13, 135.39, 127.01, 122.19, 120.26, 32.01, 30.29, 29.43, 23.01, 14.24.

Provenance & Evidence