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

HRID 1897396노트

반응식

HRID 1897396 반응식
[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]

참가 물질

6

반응물 4

HCID 8058HexaneHCID 15096Tributyltin ChlorideHCID 59426893HCID 59426893, 화합물HCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-285defcc70a34d9096be0fc79034af18
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08519087B2

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