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

HRID 646542Notes

Reaction equation

HRID 646542 reaction equation
[CH2:1]([C:7]1[C:8]2[S:17][CH:16]=[CH:15][C:9]=2[S:10][C:11]=1C(O)=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].N1C2C(=CC=CC=2)C=CC=1.C(=O)=O>[Cu].CCCCCC>[CH2:1]([C:7]1[C:8]2[S:17][CH:16]=[CH:15][C:9]=2[S:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 7047QuinolineHCID 16103482HCID 16103482, compound

Product 1

HCID 161034513-Hexylthieno[3,2-b]thiopheneYield 207.2%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8058HexaneSolvent

Conditions

Temperature
260 °C

Procedure

A mixture of compound 62 (14.6 g, 0.054 mol), copper powder (2.00 g), and quinoline (80 mL) was heated at about 260° C. in a Woods metal bath. When no further bubbles of CO2 were detected (about 2 hours), the mixture was allowed to cool to room temperature, and hexane (200 mL) was added. The mixture was washed repeatedly with HCL (1-2 M in water) to remove the quinoline. The organic layer was dried over MgSO4 and concentrated by evaporation. The residue was purified by column chromatography (SiO2/hexanes) to yield compound 58 (25.1 g, 90.3%). 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.

Workup

  1. custom(about 2 hours)
  2. temperatureto cool to room temperature
  3. washThe mixture was washed repeatedly with HCL (1-2 M in water)
  4. customto remove the 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-30cc83f07cd24fdba8d7f9d80ac88dc0
Source dataset
uspto-grants-2010_04
Patent number
US07705108B2

Reaction notes

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