Tributylstannane → HCID 21833714, compound

HRID 1741082Notes

Reaction equation

HRID 1741082 reaction equation
I[C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[O:4][CH2:5][CH2:6][C:7]1[CH2:8][CH2:9][N:10]([CH3:13])[CH2:11][CH:12]=1.C([SnH](CCCC)CCCC)CCC>C1C=CC=CC=1.CC(N=NC(C#N)(C)C)(C#N)C>[CH3:13][N:10]1[CH2:9][CH2:8][C:7]2([C:2]3[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=3[O:4][CH2:5][CH2:6]2)[CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 5948Tributylstannane2×HCID 21833858HCID 21833858, compound

Product 1

HCID 21833714HCID 21833714, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalyst2×HCID 241BenzeneSolvent2×

Procedure

A stirred solution of 4-(2-(2-iodophenoxy)ethyl)-1-methyl-1,2,3,6-tetrahydropyridine (D100, 6.3 g, 0.018 mole) and AIBN (50 mg) in benzene (700 ml) was heated to reflux under argon, then treated dropwise over 1 h with a solution of tributyltin hydride (9.7 ml, 0.036 mole) in benzene (100 ml). The reaction mixture was heated under reflux for a further 3 h after completing the addition, then more tributyltin hydride (3.8 ml, 0.014 mole) and AIBN (30 mg) were added and heating under reflux was continued for 4 h. The reaction mixture was allowed to cool, then concentrated in vacuo and the residue treated with 2M HCl acid (150 ml), washed with ethyl acetate (100 ml), basified with potassium carbonate and extracted with ethyl acetate (2×100 ml). The combined extract was dried (Na2SO4) and concentrated in vacuo to leave a yellow oil, which was chromatographed on silica gel eluting with 0 to 2% methanol/chloroform to afford the title compound (2.3 g of approx. 86% purity, 51%).

Workup

  1. temperatureto reflux under argon
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for a further 3 h
  4. additionthe addition
  5. temperatureheating
  6. temperatureunder reflux
  7. temperatureto cool
  8. concentrationconcentrated in vacuo
  9. additionthe residue treated with 2M HCl acid (150 ml)
  10. washwashed with ethyl acetate (100 ml)
  11. extractionextracted with ethyl acetate (2×100 ml)
  12. extractionThe combined extract
  13. dry with materialwas dried (Na2SO4)
  14. concentrationconcentrated in vacuo
  15. customto leave a yellow oil, which
  16. customwas chromatographed on silica gel eluting with 0 to 2% methanol/chloroform

Sources & evidence

ORD record
ord-f37c6a4d945f4e0584a8da9c4f0ce952
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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