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

HRID 440764Notes

Reaction equation

HRID 440764 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.C([Li])CCC.[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]>CCOCC>[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

5

Reactant 3

HCID 8030ThiopheneHCID 15096Tributyltin ChlorideHCID 178418339Butyllithium

Product 1

HCID 27793732-(Tri-n-butylstannyl)thiophene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 8.4 g of thiophene in 200 ml of ether is stirred, cooled to 0° C. under nitrogen while 48.0 g of butyl lithium is added dropwise via syringe. After stirring for 1 hour, the reaction mixture is cooled to -78° C. and 35.0 ml of tributyl tin chloride is added dropwise via syringe. Following stirring at room temperature for 30 minutes, the reaction mixture is quenched with 60 ml of water, poured over crushed ice and extracted with ether (3×200 ml). The organic layer is dried and evaporated in vacuo to give 46.2 g of the desired product as a residue.

Workup

  1. additionis added dropwise via syringe
  2. stirringFollowing stirring at room temperature for 30 minutes
  3. customthe reaction mixture is quenched with 60 ml of water
  4. additionpoured
  5. customover crushed ice
  6. extractionextracted with ether (3×200 ml)
  7. customThe organic layer is dried
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-8e91c187d37e4b0983464bc5d9d2f8b4
Source dataset
uspto-grants-1996_05
Patent number
US05521173

Reaction notes

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