Thiophene → 2,5-Diheptylthiophene

HRID 1720751

反応式

HRID 1720751 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[Li][CH2:7][CH2:8][CH2:9][CH3:10].[CH3:11][CH2:12][CH2:13]CCC.Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C1COCC1>[CH2:10]([C:2]1[S:1][C:5]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:4][CH:3]=1)[CH2:9][CH2:8][CH2:7][CH2:11][CH2:12][CH3:13]

参加物

6

反応物 4

HCID 8030ThiopheneHCID 8058HexaneHCID 123691-BromoheptaneHCID 178418339Butyllithium

生成物 1

HCID 6071142,5-Diheptylthiophene収率 76%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

In a typical experiment, 2 g (0.024 mole) of thiophene in 50 ml THF (dried over sodium) were treated with 2.5 eq. 1.5M n-BuLi in hexane (0.06 mole, 45 ml) at 0° C. When addition was completed, the mixture was stirred at room temperature for 5 hours. The solution was cooled at 0° C., quenched with 9.5 ml (0.06 mole) of 1-bromoheptane and then stirred at room temperature for 24 hours. The mixture was poured into ice, extracted with ether, dried (MgSO4), and the solvent evaporated. The crude product contains mono and disubstituted thiophene in the ratio 1:2 (by 1H-nmr). The crude product was then treated under the same conditions as above to yield exclusively 2,5-diheptylthiophene (5.1 g, 76%) bp 225°/0.1 mm. 1H-nmr (CDCl3) shows 86.5 (s, 2H); 2.7 (t, 4H); 0.75-2.0 (M, 26H).

後処理

  1. customat 0° C
  2. additionWhen addition
  3. temperatureThe solution was cooled at 0° C.
  4. stirringstirred at room temperature for 24 hours
  5. additionThe mixture was poured into ice
  6. extractionextracted with ether
  7. dry with materialdried (MgSO4)
  8. customthe solvent evaporated
  9. additionThe crude product was then treated under the same conditions as above

出典と根拠

ORDレコード
ord-53a7dc38df7445789e32d97ca0ce44a8
出典データセット
uspto-grants-1996_04
特許番号
US05506708

関連ノート

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