Tributyltin Chloride → 4-(Tributylstannyl)-1-tritylimidazole

HRID 428948Notes

Reaction equation

HRID 428948 reaction equation
I[C:2]1[N:3]=[CH:4][N:5]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=1.C([Mg]Br)C.[CH2:30]([Sn:34](Cl)([CH2:39][CH2:40][CH2:41][CH3:42])[CH2:35][CH2:36][CH2:37][CH3:38])[CH2:31][CH2:32][CH3:33]>ClCCl>[CH2:39]([Sn:34]([CH2:30][CH2:31][CH2:32][CH3:33])([CH2:35][CH2:36][CH2:37][CH3:38])[C:2]1[N:3]=[CH:4][N:5]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=1)[CH2:40][CH2:41][CH3:42]

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 6182524-Iodo-1-tritylimidazoleHCID 178418443HCID 178418443, compound

Product 1

HCID 118281174-(Tributylstannyl)-1-tritylimidazoleYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-iodo-1-triphenylmethyl-1H-imidazole (Preparation 72, 0.44 g, 0.10 mmol) in dichloromethane (8.0 ml) at room temperature was added slowly ethyl magnesium bromide (3.0 M in diethyl ether, 0.35 ml, 1.0 mmol). After 30 min, tributyltin chloride (0.3 ml, 1.1 immol) was added and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was quenched with saturated aqueous ammonium chloride solution (10 ml) and the product was extracted with dichloromethane (3×10 ml). The combined organic layers were dried (Na2SO4) and concentrated inl vacuo. The residue was purified by flash chromatography on silica gel eluting with hexane:ethyl acetate (10:1 and then 5:1) to give the title compound (59 mg, 98%).

Workup

  1. customThe reaction mixture was quenched with saturated aqueous ammonium chloride solution (10 ml)
  2. extractionthe product was extracted with dichloromethane (3×10 ml)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated inl vacuo
  5. customThe residue was purified by flash chromatography on silica gel eluting with hexane:ethyl acetate (10:1

Sources & evidence

ORD record
ord-d22e3d04a89e4c53878e66d55b285fe7
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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