Hexane → 3-(Tributylstannyl)pyridine

HRID 1359271Notes

Reaction equation

HRID 1359271 reaction equation
CCCCCC.C([Li])CCC.Br[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.[CH2:19]([Sn:23](Cl)([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH3:22]>O>[N:15]1[CH:16]=[CH:17][CH:18]=[C:13]([Sn:23]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:19][CH2:20][CH2:21][CH3:22])[CH:14]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 122863-BromopyridineHCID 15096Tributyltin ChlorideHCID 178418339Butyllithium

Product 1

HCID 34838483-(Tributylstannyl)pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.45 ml of a hexane solution containing 1.54 M normal butyl lithium was added dropwise into 200 ml of diethyl solution containing 10.0 g of 3-bromopyridine at −78° C. in a nitrogen atmosphere over 10 minutes. After the dropwise addition, the mixture was stirred for 10 minutes and then 20 ml of tributyltin chloride was added dropwise thereinto over 10 minutes. Then, after stirring for 30 minutes, water was added to the reaction mixture and then extracted with ethyl acetate. The extract was washed with brine and the solvent was removed. The residue was subjected to silica column chromatography and eluted with hexane and then with hexane/ethyl acetate (7:1), to give 21.9 g of the target compound.

Workup

  1. additionwas added dropwise into 200 ml of diethyl solution
  2. additionAfter the dropwise addition
  3. waitover 10 minutes
  4. stirringThen, after stirring for 30 minutes
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with brine
  7. customthe solvent was removed
  8. washeluted with hexane

Sources & evidence

ORD record
ord-dca53bea8acf41d2b382dd614a80ae35
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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