Pentane → Stannane, trimethyl-2-thienyl-

HRID 263839Notes

Reaction equation

HRID 263839 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.C([Li])(C)(C)C.CCCCC.[CH3:16][Sn:17](Cl)([CH3:19])[CH3:18]>C1COCC1>[CH3:16][Sn:17]([CH3:19])([CH3:18])[C:2]1[S:1][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8003PentaneHCID 8030ThiopheneHCID 14016Trimethyltin chlorideHCID 178418306HCID 178418306, compound

Product 1

HCID 11746949Stannane, trimethyl-2-thienyl-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of thiophene (2.1 g, 25.0 mmol) in anhydrous THF (50 mL) was added dropwise over 30 minutes at -38 C. t-butyllithium in pentane (1.6M, 16.0 mL, 25.6 mmol). The solution was stirred for 1 h at -38 C. and then cooled to -78 C. Trimethyltin chloride in THF (1M, 25.3 mL, 25.3 mmol) was added dropwise over 30 min. The reaction was then stirred for 2 h at-78 C. and then for 15 h at r.t. The solvent was evaporated and the resulting yellow solid was taken up in ether, washed with water and dried Na2SO4 and then evaporated to give a light brown liquid which solidified on standing.

Workup

  1. temperatureand then cooled to -78 C
  2. stirringThe reaction was then stirred for 2 h at-78 C
  3. waitand then for 15 h at r.t
  4. customThe solvent was evaporated
  5. washwashed with water and dried Na2SO4
  6. customevaporated
  7. customto give a light brown liquid which

Sources & evidence

ORD record
ord-89276d34e8fa4aecb773e5ab9b4d8b79
Source dataset
uspto-grants-1997_07
Patent number
US05645985

Reaction notes

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