Tributyltin Chloride → 1-Methyl-4-(tributylstannyl)-1H-pyrazole

HRID 2307391Notes

Reaction equation

HRID 2307391 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[N:9][N:10]([CH3:12])[CH:11]=1.[CH2:13]([Sn:17](Cl)([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH3:16]>C(OCC)C>[CH3:12][N:10]1[CH:11]=[C:7]([Sn:17]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:13][CH2:14][CH2:15][CH3:16])[CH:8]=[N:9]1

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 1674331H-Pyrazole, 4-bromo-1-methyl-HCID 178418339Butyllithium

Product 1

HCID 105712381-Methyl-4-(tributylstannyl)-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent4×

Procedure

To a precooled (<−10° C. internal temperature) solution of 1.6M n-butyl lithium in hexanes (100 ml) in anhydrous diethyl ether (100 ml) under argon was added a solution of 4-bromo-1-methyl-1H-pyrazole (23.42 g) from Example 111 in diethyl ether (50 ml) at a rate to maintain the temperature. The reaction was allowed to stir for a further 20 minutes before tributyltin chloride (43.4 ml) was added in diethyl ether (50 ml). The reaction temperature was allowed to rise to 20° C. The reaction was diluted with diethyl ether and the insoluble material removed by suction filtration. Evaporation of the solvent in vacuo afforded 56 g of the title compound as an oil. MS, m/z: 373 [M+H]+. Residual amounts of tin residues were removed from the oil by distillation using a kugelrohr apparatus under high vacuum at 170° C.

Workup

  1. temperatureto maintain the temperature
  2. customto rise to 20° C
  3. customthe insoluble material removed by suction filtration
  4. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-37739ce3f8b442e093e43112d81c4251
Source dataset
uspto-grants-2004_12
Patent number
US06831079B1

Reaction notes

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