Tributyltin Chloride → 2-methyl-1-phenyl-4-tributylstannanyl-1H-imidazole

HRID 1898630Notes

Reaction equation

HRID 1898630 reaction equation
I[C:2]1[N:3]=[C:4]([CH3:13])[N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=1.C([Mg]Cl)(C)C.[CH2:19]([Sn:23](Cl)([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH3:22].[NH4+].[Cl-]>C1COCC1.C(OCC)(=O)C>[CH3:13][C:4]1[N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=[C:2]([Sn:23]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:19][CH2:20][CH2:21][CH3:22])[N:3]=1

Participants

7

Reactant 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 575166484-iodo-2-methyl-1-phenyl-1H-imidazoleHCID 178418918HCID 178418918, compound

Product 1

HCID 575166502-methyl-1-phenyl-4-tributylstannanyl-1H-imidazoleYield 23.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Iodo-2-methyl-1-phenyl-1H-imidazole (0.55 g, 1.94 mmol) was dissolved in 9 mL of anhydrous THF and isopropylmagnesium chloride (2 M THF solution, 1.2 mL, 2.4 mmol) was added dropwise. The reaction was stirred for more than 1 h at room temperature. Tributylstannyl chloride (0.55 mL, 2.03 mmol) was slowly added. After the reaction was judged to be complete by TLC, NH4Cl solution and ethyl acetate were added. The layers were separated and the aqueous layer was extracted twice more with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel chromatography (triethylamine/ethyl acetate/hexanes) to give 0.2 g (23%) of 2-methyl-1-phenyl-4-tributylstannanyl-1H-imidazole.

Workup

  1. additionwere added
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted twice more with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (triethylamine/ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-464f3704f7d94c7e8066c5653b6ec4fd
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

Loading…