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

HRID 1897396Notes

Reaction equation

HRID 1897396 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-285defcc70a34d9096be0fc79034af18
Source dataset
uspto-grants-2013_08
Patent number
US08519087B2

Reaction notes

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