Trimethyltin chloride → HCID 22143620, compound

HRID 850119Notes

Reaction equation

HRID 850119 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[N:3]1.Cl[Sn:8]([CH3:11])([CH3:10])[CH3:9]>CCCCCC.C1COCC1>[CH3:1][N:2]1[C:6]([Sn:8]([CH3:11])([CH3:10])[CH3:9])=[CH:5][CH:4]=[N:3]1

Participants

5

Reactant 2

HCID 14016Trimethyltin chlorideHCID 702551H-Pyrazole, 1-methyl-

Product 1

HCID 22143620HCID 22143620, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Butylithium (2.5M in hexane, 9.75 ml, 24.4 mmol) was added to a stirred solution of 1-methylpyrazole (2.0 g. 24.4 mmol) in THF (30 ml) at -78° C. After 0.15 hours, a solution of chlorotrimethylstannane (4.85 g, 24.4 mmol) was added dropwise and the mixture allowed to warm to room temperature. The mixture was evaporated under reduced pressure and the residue partitioned between ether (50 ml) and water (50 ml). The ether layer was dried (MgSO4) and evaporated to yield the title compound as colourless oil (6.0 g, quantitative), which was characterised by 1H-NMR spectroscopy.

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. customthe residue partitioned between ether (50 ml) and water (50 ml)
  3. dry with materialThe ether layer was dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-16f1579f75d14688857a258c0a0818f7
Source dataset
uspto-grants-2000_01
Patent number
US06015825

Reaction notes

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