Water → HCID 87227725, compound

HRID 557688Notes

Reaction equation

HRID 557688 reaction equation
[CH2:1]([C:7]1([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:17]2[CH:16]=[CH:15][S:14][C:13]=2[C:9]2[S:10][CH:11]=[CH:12][C:8]1=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Li][CH2:25][CH2:26][CH2:27][CH3:28].[Sn:29](Cl)([CH2:38][CH2:39][CH2:40][CH3:41])([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:30][CH2:31][CH2:32][CH3:33].O>C1COCC1.CCCCCC.C(N(CC)CC)C>[CH2:25]([Sn:29]([C:12]1[C:8]2[C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:17]3[CH:16]=[CH:15][S:14][C:13]=3[C:9]=2[S:10][C:11]=1[Sn:29]([CH2:38][CH2:39][CH2:40][CH3:41])([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:30][CH2:31][CH2:32][CH3:33])([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH3:28]

Participants

8

Reactant 4

HCID 962WaterHCID 15096Tributyltin ChlorideHCID 594268924,4-Dihexyl-4H-cyclopenta[1,2-b:5,4-b']bisthiopheneHCID 178418339Butyllithium

Product 1

HCID 87227725HCID 87227725, compoundYield 94.8%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
-78 °C

Procedure

4,4-Dihexyl-4H-cyclopenta[2,1-b;3,4-b′]dithiophene (2.2 g, 0.0065 mol) was dissolved in dry THF (20 mL). The solution was cooled to −78° C. BuLi (7.62, 2.5 M in hexanes, 0.019 mol) was then added to the solution. The reaction mixture was allowed to warm to room temperature and was stirred for 5 hours. The mixture was then cooled again to −78° C. and Bu3SnCl (7.44g, 0.0229 mol) was added. The reaction mixture was allowed to warm to room temperature and was stirred for another 48 hours. Water was then added and the mixture was extracted with dihicholomethane. Organic layer was collected, dried over anhydrous Na2SO4, and concentrated. The residue thus obtained was dissolved in hexane and quickly passed through a plug of silica gel pretreated with triethylamine. The solvent was removed and the residue was dried under vacuum to afford bis-(tributylstannyl)-4,4-dihexyl-cyclopenta[2,1-b:3,4-b′] dithiophene (5.7 g).

Workup

  1. temperatureto warm to room temperature
  2. temperatureThe mixture was then cooled again to −78° C.
  3. temperatureto warm to room temperature
  4. stirringwas stirred for another 48 hours
  5. extractionthe mixture was extracted with dihicholomethane
  6. customOrganic layer was collected
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. customThe residue thus obtained
  10. customThe solvent was removed
  11. customthe residue was dried under vacuum

Sources & evidence

ORD record
ord-8e1adf195c9c49e2bae25b13ec465ec8
Source dataset
uspto-grants-2011_11
Patent number
US08058550B2

Reaction notes

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