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

HRID 2098188Notes

Reaction equation

HRID 2098188 reaction equation
C([Mg]Br)C.I[C:6]1[N:7]=[CH:8][N:9]([CH3:11])[CH:10]=1.[CH2:12]([Sn:16](Cl)([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH3:15]>C1COCC1>[CH3:11][N:9]1[CH:10]=[C:6]([Sn:16]([CH2:17][CH2:18][CH2:19][CH3:20])([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:12][CH2:13][CH2:14][CH3:15])[N:7]=[CH:8]1

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 27734634-Iodo-1-methyl-1H-imidazoleHCID 178418443HCID 178418443, compound

Product 1

HCID 219011411-Methyl-4-(tributylstannyl)-1H-imidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3 M Ethyl magnesium bromide in THF (11.0 ml, 33.0 mmol) was added dropwise to a solution of 4-iodo-1-methyl-1H-imidazole (5.61 g, 27.0 mmol) in THF (50 ml) at −78° C. After stirring for 2 h, tributyltin chloride (8.0 ml, 29.5 mmol) was added. After stirring for an additional 2 h, the solution was concentrated under reduced pressure. The residue was flash chromatographed (hexane:ethyl acetate) to yield 1-methyl-4-(tributylstannyl)-1H-imidazole. Method [7] Retention time 7.34 min by HPLC (MH+ 373).

Workup

  1. stirringAfter stirring for an additional 2 h
  2. concentrationthe solution was concentrated under reduced pressure
  3. customchromatographed (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-376ae8ad10144f099e5103f5c162ebd1
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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