Hexane → [4,4-Bis(2-ethylhexyl)-4H-cyclopenta[1,2-b:5,4-b']bisthiene-2,6-diyl]bis(trimethylstannane)

HRID 1897396ノート

反応式

HRID 1897396 の反応式
[CH2:1]([CH:3]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:4][C:5]1([CH2:16][CH:17]([CH2:22][CH3:23])[CH2:18][CH2:19][CH2:20][CH3:21])[C:15]2[CH:14]=[CH:13][S:12][C:11]=2[C:7]2[S:8][CH:9]=[CH:10][C:6]1=2)[CH3:2].[Li]CCCC.[CH2:33]([Sn:37](Cl)([CH2:42]CCC)[CH2:38]CCC)CCC.CCCCCC>C1COCC1>[CH2:1]([CH:3]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:4][C:5]1([CH2:16][CH:17]([CH2:22][CH3:23])[CH2:18][CH2:19][CH2:20][CH3:21])[C:6]2[CH:10]=[C:9]([Sn:37]([CH3:42])([CH3:38])[CH3:33])[S:8][C:7]=2[C:11]2[S:12][C:13]([Sn:37]([CH3:42])([CH3:38])[CH3:33])=[CH:14][C:15]1=2)[CH3:2]

参加物

6

反応物 4

HCID 8058HexaneHCID 15096Tributyltin ChlorideHCID 59426893HCID 59426893、化合物HCID 178418339Butyllithium

生成物 1

HCID 44203213[4,4-Bis(2-ethylhexyl)-4H-cyclopenta[1,2-b:5,4-b']bisthiene-2,6-diyl]bis(trimethylstannane)収率 94%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

The 4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b′]dithiophene (3.0 g, 7.45 mmol) prepared above was dissolved in anhydrous THF (20 mL) and kept at −78° C. under nitrogen flow. Then, n-BuLi (19 mL, 29.8 mmol, 2.5 M in hexane) was slowly added over 30 minutes. Subsequently, after stirring at −78° C. for 1 hour, tributyltin chloride (7.4 g, 37.1 mmol) was added and reaction was performed at room temperature for 17 hours. The resulting product was extracted with ether and distilled water, dried with anhydrous MgSO4 and filtered under reduced pressure. The final product 4,4-bis(2-ethylhexyl)-2,6-bis(trimethylstannyl)-4H-cyclopenta[2,1-b:3,4-b′]dithiophene (5.1 g, yield: 94%) was obtained by column chromatography (neutral alumina, n-hexane). 1H NMR (300 MHz, CDCl3, ppm): δ 7.01-6.88 (m, 2H), 1.93-1.76 (m, 4H), 1.04-0.81 (m, 18H), 0.74 (t, 6H), 0.59 (t, 6H), 0.49-0.22 (m, 18H).

後処理

  1. customkept at −78° C. under nitrogen
  2. customreaction
  3. waitwas performed at room temperature for 17 hours
  4. extractionThe resulting product was extracted with ether
  5. distillationdistilled water
  6. dry with materialdried with anhydrous MgSO4
  7. filtrationfiltered under reduced pressure

出典と根拠

ORDレコード
ord-285defcc70a34d9096be0fc79034af18
出典データセット
uspto-grants-2013_08
特許番号
US08519087B2

反応ノート

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