Thiophene → 2-(Tri-n-butylstannyl)thiophene

HRID 1897398Notes

Reaction equation

HRID 1897398 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[Li]CCCC.[CH2:11]([Sn:15](Cl)([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH3:14].CCCCCC>C1COCC1>[CH2:20]([Sn:15]([CH2:11][CH2:12][CH2:13][CH3:14])([CH2:16][CH2:17][CH2:18][CH3:19])[C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 8030ThiopheneHCID 8058HexaneHCID 15096Tributyltin ChlorideHCID 178418339Butyllithium

Product 1

HCID 27793732-(Tri-n-butylstannyl)thiopheneYield 55.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Thiophene (2.0 g, 12 mmol) was dissolved in anhydrous THF (20 mL) and n-BuLi (9.52 mL, 23.8 mmol, 2.5 M in hexane) slowly added at −30° C. under nitrogen flow. After stirring for 1 hour, tributyltin chloride (7.75 mL, 23.8 mmol) was added. After heating to room temperature, followed by stirring for 3 hours, the reaction was terminated. The produced compound was extracted with n-hexane and distilled water, dried with anhydrous MgSO4 and filtered under reduced pressure. The final product tributyl-2-thienylstannane (2.5 g, yield: 46%) was obtained by column chromatography (neutral alumina, n-hexane). The product was used in the next step after removing the solvent.

Workup

  1. stirringby stirring for 3 hours
  2. customthe reaction was terminated
  3. extractionThe produced compound was extracted with n-hexane
  4. distillationdistilled water
  5. dry with materialdried with anhydrous MgSO4
  6. filtrationfiltered under reduced pressure

Sources & evidence

ORD record
ord-bf304fdb6fde4673b4096fc2d1da5f6e
Source dataset
uspto-grants-2013_08
Patent number
US08519087B2

Reaction notes

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