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

HRID 1594063Notes

Reaction equation

HRID 1594063 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 [available via the procedure outlined in Tang, C. C.; Davalian, D.; Huang, P.; Breslow, R. J. Am. Chem. Soc. 1978, 100, 3918] (2.20 g, 17.4 mmol) in THF (30 mL) at −78° C. under N2. The reaction mixture is stirred at −78° C. for 20 min. whereupon tributyltin chloride (5.7 mL, 20.9 mmol) is slowly added. The reaction mixture is stirred at −78° C. for 10 min. and then warmed to room temperature. After stirring at room temperature for 1.5 h, 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. customat −78° C.
  2. additionis slowly added
  3. temperaturewarmed to room temperature
  4. stirringAfter stirring at room temperature for 1.5 h
  5. concentrationthe reaction mixture is concentrated in vacuo
  6. customThe residue is triturated with hexanes
  7. filtrationfiltered
  8. concentrationthe filtrate is concentrated in vacuo
  9. customThe residue is again triturated with hexanes
  10. filtrationfiltered
  11. concentrationthe filtrate concentrated in vacuo
  12. additiona 2:1 mixture of 1-ethoxymethyl-2-tributylstannanyl-1H-imidazole
  13. customThis material is used in the next reaction without further purification

Sources & evidence

ORD record
ord-ad31e4d9d5d54465b34db20019281358
Source dataset
uspto-grants-2007_11
Patent number
US07300945B2

Reaction notes

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