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

HRID 2098191Notes

Reaction equation

HRID 2098191 reaction equation
C([Mg]Br)C.I[C:6]1[N:7]=[CH:8][N:9]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=1.[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]>C1COCC1>[CH2:39]([Sn:34]([CH2:30][CH2:31][CH2:32][CH3:33])([CH2:35][CH2:36][CH2:37][CH3:38])[C:6]1[N:7]=[CH:8][N:9]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=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 126.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3 M Ethyl magnesium bromide in THF (5.0 ml, 15.0 mmol) was added dropwise to a solution of 4-iodo-1-trityl-1H-imidazole (4.44 g, 10.2 mmol) in THF (100 ml) at −78° C. After stirring for 2 h, tributyltin chloride (5.0 ml, 18.4 mmol) was added. After stirring for an additional 2 h, the solution was concentrated under reduced pressure. The residue was flash chromatographed with 19:1, 9:1, 17:3, and 4:1 hexane:ethyl acetate as the eluant to yield 7.72 g of impure 4-(tributylstannyl)-1-trityl-1H-imidazole as a yellow solid. Method [7] Retention time 10.89 min by HPLC (MH+ 601).

Workup

  1. stirringAfter stirring for an additional 2 h
  2. concentrationthe solution was concentrated under reduced pressure
  3. customchromatographed with 19:1, 9:1, 17:3, and 4:1 hexane

Sources & evidence

ORD record
ord-dcd676ae7dbc460f9ab3c0b41a300ca2
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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