1-Methylimidazole → 1-Methyl-2-(tributylstannyl)-1H-imidazole

HRID 2061113Notes

Reaction equation

HRID 2061113 reaction equation
[Li]CCCC.[CH3:6][N:7]1[CH:11]=[CH:10][N:9]=[CH:8]1.[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]>O1CCCC1>[CH3:6][N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[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]

Participants

5

Reactant 3

HCID 13901-MethylimidazoleHCID 15096Tributyltin ChlorideHCID 178418339Butyllithium

Product 1

HCID 27632521-Methyl-2-(tributylstannyl)-1H-imidazoleYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-BuLi (7.6 mL, 18.9 mmol) was added dropwise at −10° C. under nitrogen atmosphere over a period of 30 minutes to an anhydrous tetrahydrofuran solution (20 mL) of 1-methyl-1H-imidazole (1.6 mL, 18.8 mmol), and the mixture was stirred for 2.5 hours. Next, a tetrahydrofuran solution (12 mL) of Bu3SnCl (5.1 mL, 18.8 mmol) was added dropwise over a period of one hour at −78° C., and then the mixture was raised to room temperature and stirred overnight. The title compound (5.48 g, 79%) was obtained by vacuum distillation (140-142° C., 0.5 mmHg).

Workup

  1. stirringstirred overnight

Sources & evidence

ORD record
ord-8893641130e54a34a7adfd803419d39a
Source dataset
uspto-grants-2012_10
Patent number
US08278465B2

Reaction notes

Loading…