Tributyltin Chloride → 1-ethoxymethyl-2-tributylstannanyl-1H-imidazole

HRID 1609837Notes

Reaction equation

HRID 1609837 reaction equation
[Li]CCCC.[CH2:6]([O:8][CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1)[CH3:7].[CH2:15]([Sn:19](Cl)([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH3:18]>C1COCC1>[CH2:6]([O:8][CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[C:11]1[Sn:19]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:15][CH2:16][CH2:17][CH3:18])[CH3:7]

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 130194491-(Ethoxymethyl)-1H-imidazoleHCID 178418339Butyllithium

Product 1

HCID 222603931-ethoxymethyl-2-tributylstannanyl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

1.6 M n-BuLi (12.0 mL, 19.2 mmol) is slowly added to a solution of 1-ethoxymethyl-1H-imidazole (2.20 g, 17.4 mmol; prepared essentially as described by Tang, et al. (1978) J. Am. Chem. Soc. 100:3918) in THF (30 mL) at −78° C. under N2. The reaction mixture is stirred at −78° C. for 20 minutes, whereupon tributyltin chloride (5.7 mL, 20.9 mmol) is slowly added. The reaction mixture is stirred at −78° C. for 10 minutes, and then warmed to room temperature. After stirring at room temperature for 1.5 hours, the reaction mixture is concentrated in vacuo. The residue is triturated with hexanes and filtered, and the filtrate is concentrated in vacuo. The residue is again triturated with hexanes and filtered, and the filtrate concentrated in vacuo. The 1H NMR of the resulting oil indicates a 2:1 mixture of 1-ethoxymethyl-2-tributylstannanyl-1H-imidazole: 1-ethoxymethyl-1H-imidazole. This material is used in the next reaction without further purification. Selected 1H NMR resonances (400 MHz, CDCl3) δ 7.21 (s, 1H), 7.14 (s, 1H), 5.24 (s, 2H) ppm.

Workup

  1. customprepared essentially
  2. customat −78° C.
  3. additionis slowly added
  4. temperaturewarmed to room temperature
  5. stirringAfter stirring at room temperature for 1.5 hours
  6. concentrationthe reaction mixture is concentrated in vacuo
  7. customThe residue is triturated with hexanes
  8. filtrationfiltered
  9. concentrationthe filtrate is concentrated in vacuo
  10. customThe residue is again triturated with hexanes
  11. filtrationfiltered
  12. concentrationthe filtrate concentrated in vacuo
  13. additiona 2:1 mixture of 1-ethoxymethyl-2-tributylstannanyl-1H-imidazole
  14. customThis material is used in the next reaction without further purification

Sources & evidence

ORD record
ord-1f0b7b19356f4272b6f463def761abd9
Source dataset
uspto-grants-2006_01
Patent number
US06982268B2

Reaction notes

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