Carbon Dioxide → HCID 16103488, compound

HRID 646543Notes

Reaction equation

HRID 646543 reaction equation
[CH2:1]([C:11]1[C:18]2[S:17][C:16]3[C:19]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[C:20](C(O)=O)[S:21][C:15]=3[C:14]=2[S:13][C:12]=1C(O)=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].N1C2C(=CC=CC=2)C=CC=1.C(=O)=O>[Cu].CCCCCC>[CH2:1]([C:11]1[C:18]2[S:17][C:16]3[C:19]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:20][S:21][C:15]=3[C:14]=2[S:13][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 7047QuinolineHCID 161034573,5-Didecanyldithieno[3,2-b:2',3'-d]thiophene-2,6-dicarboxylic acid

Product 1

HCID 16103488HCID 16103488, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8058HexaneSolvent

Conditions

Temperature
255 °C

Procedure

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.

Workup

  1. custom(about 2 hours)
  2. temperaturethe mixture was cooled to room temperature
  3. washThis mixture was washed repeatedly with HCl (1-2 M in water)
  4. customto remove quinoline
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated by evaporation
  7. customthe residue was purified by column chromatography (SiO2/hexanes)

Sources & evidence

ORD record
ord-a30762a7610d448b91ac73b073f7f522
Source dataset
uspto-grants-2010_04
Patent number
US07705108B2

Reaction notes

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