Tributyltin Chloride → 1-methyl-5-(tributylstannyl)-1H-1,2,3-triazole

HRID 1894089Notes

Reaction equation

HRID 1894089 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[N:3]1.[Li]CCCC.[Sn:12](Cl)([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH2:15][CH3:16]>C1COCC1>[CH3:1][N:2]1[C:6]([Sn:12]([CH2:17][CH2:18][CH2:19][CH3:20])([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:13][CH2:14][CH2:15][CH3:16])=[CH:5][N:4]=[N:3]1

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 1401191-Methyl-1H-1,2,3-triazoleHCID 178418339Butyllithium

Product 1

HCID 226098261-methyl-5-(tributylstannyl)-1H-1,2,3-triazoleYield 102.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-methyl-1H-[1,2,3]triazole (1.33 g, 16 mmol) in THF (20 mL) at −78° C., was added dropwise n-BuLi (11 mL, 1.6M, 18 mmol). The mixture was stirred at −78° C. for 2 h before addition of Bu3SnCl (4.75 mL, 17.6 mmol). The mixture was stirred at this temperature for 1 h and at r.t. for 1 h. The mixture was concentrated in vacuo and hexanes was added. The insoluble material was removed by filtration and the filtrate was concentrated in vacuo to afford 1-methyl-5-tributylstannanyl-1H-[1,2,3]triazole (6.12 g, 82% yield) as a yellow syrup.

Workup

  1. concentrationThe mixture was concentrated in vacuo and hexanes
  2. additionwas added
  3. customThe insoluble material was removed by filtration
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-83fd71c82f47402e8896491e294208da
Source dataset
uspto-grants-2013_08
Patent number
US08513268B2

Reaction notes

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