Trimethyltin chloride → HCID 22143620, compound

HRID 985197Notes

Reaction equation

HRID 985197 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[N:3]1.C([Li])CCC.[CH3:12][Sn:13](Cl)([CH3:15])[CH3:14]>CCOCC>[CH3:1][N:2]1[C:6]([Sn:13]([CH3:15])([CH3:14])[CH3:12])=[CH:5][CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 14016Trimethyltin chlorideHCID 702551H-Pyrazole, 1-methyl-HCID 178418339Butyllithium

Product 1

HCID 22143620HCID 22143620, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 1-methyl-1H-pyrazole (1.6 g, 20.0 mmole) in Et2O was treated with n-butyllithium (12.5 ml, 1.6 M in hexanes, 20.0 mmole) over a period of 10 minutes at room temperature. The yellow slurry was stirred for a further 90 minutes. Subsequently, trimethyltin chloride (4.0 g, 20.0 mmole) was added in one portion. The brown slurry was stirred for 30 minutes, filtered and the filtrate was concentrated, in vacuo, to a black oil (5.0 g). The product was isolated by distillation at 1.5 Torr (67-72° C.) as a clear oil (2.1 g, 42%): 1H-NMR (DMSO-d6, 400 MHz) δ7.40 (1H, d, J=1.5 Hz), 6.27 (1H, d, J=1.7 Hz), 3.84 (3H, s), 0.34 (9H, s). ESIMS m/z 243-247 ion cluster (M+H)+.

Workup

  1. stirringThe brown slurry was stirred for 30 minutes
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated, in vacuo, to a black oil (5.0 g)

Sources & evidence

ORD record
ord-7605974e442346fe8e83269637b8014d
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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