Tributyltin Chloride → 2-(4-Methoxyphenyl)-6,7-dihydro-[5H]-pyrrolo[1,2-a]imidazol-3-yl-tri-n-butyltin

HRID 1885582Notes

Reaction equation

HRID 1885582 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]3[CH2:16][CH2:15][CH2:14][N:12]3[CH:13]=2)=[CH:5][CH:4]=1.C([Li])CCC.[CH2:22]([Sn:26](Cl)([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH3:25].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]=[C:11]3[CH2:16][CH2:15][CH2:14][N:12]3[C:13]=2[Sn:26]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:22][CH2:23][CH2:24][CH3:25])=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 9101232-(4-methoxyphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazoleHCID 178418339Butyllithium

Product 1

HCID 198792232-(4-Methoxyphenyl)-6,7-dihydro-[5H]-pyrrolo[1,2-a]imidazol-3-yl-tri-n-butyltinYield 49%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent2×

Procedure

To an ice cold (0° C.) solution of [16.8 g, 0.078 mol] 2-(4-methoxyphenyl)-6,7-dihydro-[5H]-pyrrolo[1,2-a]imidazole in 200 ml of dry tetrahydrofuran under argon was added dropwise over 20 minutes 35 mL [0.0858 mol] of a 2.5M solution of n-butyl lithium in hexane. Once the addition was complete, the deep-red solution was stirred in the cold for five minutes and then a solution of the tributyltin chloride [26.4 g, 0.0975 mol] in 50 ml of dry tetrahydrofuran was added over 20 min. The reaction mixture was stirred at ice-bath temperatures for 1.5 hours and then saturated ammonium chloride was added. The layers were shaken together and separated and the organic extract was washed an additional time with saturated ammonium chloride and then dried with anhydrous potassium carbonate. The solvent was removed in vacuo to give 50 g of a crude oil, which was taken up twice in cold hexane, filtering off the unreacted 2-(4-methoxyphenyl)-6,7-dihydro-[5H]-pyrrolo[1,2-a]imidazole each time. The product was purified on a column of silica, eluting with 1:1 ethyl acetate/hexane in the presence of 1% diethylamine, to give 19.2 g (49% of a yellow oil.

Workup

  1. additionOnce the addition
  2. stirringThe reaction mixture was stirred at ice-bath temperatures for 1.5 hours
  3. stirringThe layers were shaken together
  4. customseparated
  5. extractionthe organic extract
  6. washwas washed an additional time with saturated ammonium chloride
  7. dry with materialdried with anhydrous potassium carbonate
  8. customThe solvent was removed in vacuo
  9. customto give 50 g of a crude oil, which
  10. filtrationfiltering off the unreacted 2-(4-methoxyphenyl)-6,7-dihydro-[5H]-pyrrolo[1,2-a]imidazole each time
  11. customThe product was purified on a column of silica
  12. washeluting with 1:1 ethyl acetate/hexane in the presence of 1% diethylamine

Sources & evidence

ORD record
ord-b786127d507e4d50bcecb5a35b61740f
Source dataset
uspto-grants-1992_09
Patent number
US05145858

Reaction notes

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