Tributyltin Chloride → 2-Methoxy-6-(tributylstannyl)pyridine

HRID 1174308Notes

Reaction equation

HRID 1174308 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[N:3]=1.C([Li])CCC.[CH2:15]([Sn:19](Cl)([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH3:18]>CCOCC>[CH2:24]([Sn:19]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:20][CH2:21][CH2:22][CH3:23])[C:2]1[N:3]=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][CH:7]=1)[CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 2568102-Bromo-6-methoxypyridineHCID 178418339Butyllithium

Product 1

HCID 105248912-Methoxy-6-(tributylstannyl)pyridine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A solution containing 2-bromo-6-methoxypyridine (0.65 mL, 5.3 mmol) in ether (11 mL) at −78° C. was treated with n-butyllithium (4.0 mL, 1.6 M in hexanes) dropwise, warmed to 0° C. for 10 minutes, cooled to −78° C., treated with tributyltin chloride (2.25 mL, 8.30 mmol), stirred at −78° C. for 0.5 hours, and then at 0° C. for 0.5 hours. The reaction was quenched with saturated ammonium chloride solution and partitioned between ether and water. The organic phase was washed with brine and dried over MgSO4, filtered and concentrated to give the title compound.

Workup

  1. temperaturecooled to −78° C.
  2. waitat 0° C. for 0.5 hours
  3. customThe reaction was quenched with saturated ammonium chloride solution
  4. custompartitioned between ether and water
  5. washThe organic phase was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-dd34e143ba624d4cae6ba18b6e66674d
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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