Carbon Dioxide → 3,6-Dihexylthieno[3,2-b]thiophene

HRID 646539Notes

Reaction equation

[CH2:1]([C:7]1[C:8]2[S:17][CH:16]=[C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[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>[CH2:18]([C:15]1[C:9]2[S:10][CH:11]=[C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:8]=2[S:17][CH:16]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

Conditions

Temperature: 262 °C

Procedure

A mixture of compound 55 (30 g, 0.085 mol), copper powder (3.76 g) and quinoline (80 mL) was heated at 264-260° C. in a Woods metal bath. When no further bubbles of carbon dioxide gas could be detected (about 2 hours), the mixture was allowed to cool to room temperature and hexane (200 mL) was added. This mixture was washed repeatedly with HCl (1-2 M in water) to remove the quinoline. The remaining organic layer was dried over MgSO4 and concentrated by evaporation, leaving a residue, which was purified by column chromatography (SiO2/hexanes) to yield compound 57 (18 g, 68.4%). m.p. 57.5-59.1° C., 1H NMR (CD2Cl2): δ 6.97 (s, 2H), 2.70 (t, 4H), 1.73 (m, 4H), 1.37 (m, 12H), 0.88 (t, 6H). 13C NMR: 136.56, 134.96, 109.80, 31.94, 29.31, 29.28, 28.47, 22.96, 14.22.

Workup

custom(about 2 hours)
temperatureto cool to room temperature
washThis mixture was washed repeatedly with HCl (1-2 M in water)
customto remove the quinoline
dry with materialThe remaining organic layer was dried over MgSO4
concentrationconcentrated by evaporation
customleaving a residue, which
customwas purified by column chromatography (SiO2/hexanes)

Sources & evidence

ORD record: ord-094d31f516ac4403ba1ffde2bebe3bc5
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705108B2

Reaction notes

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