Tributylstannane → HCID 21833714, 화합물

HRID 617733노트

반응식

HRID 617733 반응식
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

참가 물질

5

반응물 2

HCID 5948Tributylstannane2회HCID 21833858HCID 21833858, 화합물

생성물 1

HCID 21833714HCID 21833714, 화합물수율 58.8%

시약·촉매·용매 2

HCID 6547Azobisisobutyronitrile촉매2회HCID 241Benzene용매2회

실험 절차

A stirred solution of 4-(2-(2-iodophenoxy)ethyl)-1-methyl-1,2,3,6tetrahydropyridine (D2, 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%).

후처리

  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

출처 및 근거

ORD 기록
ord-dcdedba2becb485cad7d3141a12d510a
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05952325

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