Tetrahydrofuran → 5,10-Bis-(2-butyl-octyloxy)-2,7-bis-trimethylstannanyl-1,6-dithia-dicyclopenta[a,f]naphthalene

HRID 628226ノート

反応式

HRID 628226 の反応式
[CH2:1]([CH:5]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:6][O:7][C:8]1[C:9]2[S:36][CH:35]=[CH:34][C:10]=2[C:11]2[CH:12]=[C:13]([O:21][CH2:22][CH:23]([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:14]3[S:20][CH:19]=[CH:18][C:15]=3[C:16]=2[CH:17]=1)[CH2:2][CH2:3][CH3:4].C1COCC1.[Li+].CCC[CH2-].[CH3:53][Sn:54](Cl)([CH3:56])[CH3:55]>CCCCCC>[CH2:30]([CH:23]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][O:21][C:13]1[C:14]2[S:20][C:19]([Sn:54]([CH3:56])([CH3:55])[CH3:53])=[CH:18][C:15]=2[C:16]2[CH:17]=[C:8]([O:7][CH2:6][CH:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[C:9]3[S:36][C:35]([Sn:54]([CH3:56])([CH3:55])[CH3:53])=[CH:34][C:10]=3[C:11]=2[CH:12]=1)[CH2:31][CH2:32][CH3:33]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 14016Trimethyltin chlorideHCID 61028n-Butyl lithiumHCID 71245667HCID 71245667、化合物

生成物 1

HCID 866966245,10-Bis-(2-butyl-octyloxy)-2,7-bis-trimethylstannanyl-1,6-dithia-dicyclopenta[a,f]naphthalene収率 79.1%

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

5,10-Bis-(2-butyl-octyloxy)-1,6-dithia-dicyclopenta[a,f]naphthalene (1.41 g, 2.3 mmol) was added into a 200 mL flask. The system was vacuumed and backfilled with argon 3 times before 60 mL of anhydrous THF was injected. N-Butyllithium (2.2 mL, 2.5 M in hexane, 5.09 mmol) was added after the mixture was cooled to −78° C. A white precipitate was observed after the mixture was stirred at −78° C. for 30 minutes. Stirring was continued at room temperature for one more hour before the mixture was cooled down to −78° C. again. Trimethyltin chloride (1.20 g, 5.75 mmol) was added in portions and stirring was continued overnight at room temperature. Hexane (100 mL) was added and the organic layer was washed with 150 mL of water. The aqueous layer was extracted with 100 mL of hexane twice. The combined organic layer was dried over anhydrous Na2SO4. Removal of solvent under vacuum yielded a white solid. The colorless crystalline product, 5,10-bis-(2-butyl-octyloxy)-2,7-bis-trimethylstannanyl-1,6-dithia-dicyclopenta[a,f]naphthalene, (1.70 g, ˜79% yield) was obtained after recrystallization from a hexane/iso-propanol mixture. 1H NMR (CDCl3, 500 MHz): δ 7.80 (s, 2H), δ 7.69 (s , 2H), δ 4.25 (d , 4H, J=5.5 Hz), δ 1.99 (m , 2H), δ 1.33 (m , 32H), δ 0.96 (t , 6H, J=7.0 Hz), δ 0.90 (t, 6H, J=7.0 Hz), δ 0.51 (m , 18H).

後処理

  1. stirringStirring
  2. customwas continued at room temperature for one more hour before the mixture
  3. temperaturewas cooled down to −78° C. again
  4. stirringstirring
  5. waitwas continued overnight at room temperature
  6. washthe organic layer was washed with 150 mL of water
  7. extractionThe aqueous layer was extracted with 100 mL of hexane twice
  8. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  9. customRemoval of solvent under vacuum
  10. customyielded a white solid

出典と根拠

ORDレコード
ord-0f04dabf8afa4697b6cd262eea367839
出典データセット
uspto-grants-2016_04
特許番号
US09312492B2

反応ノート

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