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

HRID 1942854
ノート
印刷プレビュー

反応式

HRID 1942854 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 280Carbon DioxideHCID 7047QuinolineHCID 161034853,6-Dihexylthieno[3,2-b]thiophene-2-carboxylic acid

生成物 1

HCID 161034553,6-Dihexylthieno[3,2-b]thiophene収率 68.6%

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 8058Hexane溶媒

反応条件

温度
262 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-c149390d05844c43b2955276286209b0
出典データセット
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08389669B2

反応ノート

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