Tributyltin Chloride → 2-(Tributylstannyl)-1,3-thiazole

HRID 1956326Notes

Reaction equation

HRID 1956326 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.C([Li])CCC.[CH2:12]([Sn:16](Cl)([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH3:15]>O1CCCC1>[CH2:21]([Sn:16]([CH2:12][CH2:13][CH2:14][CH3:15])([CH2:17][CH2:18][CH2:19][CH3:20])[C:2]1[S:3][CH:4]=[CH:5][N:6]=1)[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 764302-BromothiazoleHCID 178418339Butyllithium

Product 1

HCID 27632592-(Tributylstannyl)-1,3-thiazoleYield 51.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 10.0 g of 2-bromothiazole under nitrogen in 50 ml of tetrahydrofuran while cooling in a dry ice-acetone bath is added dropwise 36.6 ml of a 1.6M solution of butyl lithium via syringe. Stirring is continued for 1 hour. To the reaction mixture is added dropwise 29.8 g of tributyltin chloride in 20 ml of tetrahydrofuran. Stirred 1 additional hour. The reaction mixture is quenched with 20 ml of water and 50 ml additional water is added. After stirring for 20 minutes the reaction mixture is extracted with chloroform (3×60 ml). The organic layer is dried (Na2SO4) and evaporated in vacuo to give 11.7 g of the desired product.

Workup

  1. stirringStirred 1 additional hour
  2. customThe reaction mixture is quenched with 20 ml of water and 50 ml additional water
  3. additionis added
  4. stirringAfter stirring for 20 minutes the reaction mixture
  5. extractionis extracted with chloroform (3×60 ml)
  6. dry with materialThe organic layer is dried (Na2SO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-01898e3a0ff54f7a95778480aa82cc51
Source dataset
uspto-grants-1998_07
Patent number
US05780471

Reaction notes

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