Tributyltin Chloride → 4-(Tri-n-butylstannyl)pyridine

HRID 1901107Notes

Reaction equation

HRID 1901107 reaction equation
Cl.Br[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[Li]CCCC.[CH2:14]([Sn:18](Cl)([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH3:17].[NH4+].[Cl-]>CCOCC>[CH2:23]([Sn:18]([CH2:14][CH2:15][CH2:16][CH3:17])([CH2:19][CH2:20][CH2:21][CH3:22])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)[CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 881004-Bromopyridinium chlorideHCID 178418339Butyllithium

Product 1

HCID 27373184-(Tri-n-butylstannyl)pyridine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-30 °C

Procedure

To a suspension of 4-bromopyridine hydrochloride (1.5 g) in Et2O (20 mL) at -78° C. was added n-BuLi (6.2 mL of a 2.5M solution). After 30 min. the mixture was warmed to -30° C., tributyltin chloride (2.1 mL) was added and the mixture warmed to 0° C. Saturated NH4Cl was added and extracted with Et2O. The organics were washed with H2O, brine, dried (MgSO4) and concentrated. Chromatography (silica gel; EtOAc/hexane (15:85)) provided the title compound as an oil.

Workup

  1. temperaturethe mixture warmed to 0° C
  2. extractionextracted with Et2O
  3. washThe organics were washed with H2O, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f75560f778c54679aed3b6aa8fc04d71
Source dataset
uspto-grants-1996_11
Patent number
US05576338

Reaction notes

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