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Tributyltin Chloride → 5-(4-Methyl-2,6,7-trioxabicyclo[2,2,2]oct-1-yl)-2-[tri(n-butyl)stannyl]furan

HRID 2085946
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HRID 2085946 반응식
[CH3:1][C:2]12[CH2:9][O:8][C:5]([C:10]3[O:11][CH:12]=[CH:13][CH:14]=3)([O:6][CH2:7]1)[O:4][CH2:3]2.[Li]CCCC.[CH2:20]([Sn:24](Cl)([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH3:23]>C1COCC1>[CH3:1][C:2]12[CH2:3][O:4][C:5]([C:10]3[O:11][C:12]([Sn:24]([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:20][CH2:21][CH2:22][CH3:23])=[CH:13][CH:14]=3)([O:6][CH2:7]1)[O:8][CH2:9]2
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참가 물질

5

반응물 3

HCID 15096Tributyltin ChlorideHCID 226097422-(4-Methyl-2,6,7-trioxabicyclo[2,2,2]oct-1-yl)furanHCID 178418339Butyllithium

생성물 1

HCID 226097085-(4-Methyl-2,6,7-trioxabicyclo[2,2,2]oct-1-yl)-2-[tri(n-butyl)stannyl]furan수율 95.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

2-(4-Methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)furan (2.0 g, 10.2 mmol) was dissolved in THF (20 ml) and the solution was cooled to −78° C. n-BuLi (1.6M solution in hexanes, 7.7 ml, 12.32mmol) was added and the mixture stirred at −78° C. for 30 min, allowed to warm to 0° C. for 20 min. and then recooled to −78° C. The tributyltin chloride (3.5 ml, 4.68 g, 14.4 mmol) was added and stirring was continued at −78° C. for 15min. The mixture was allowed to warm gradually to room temperature and stirring continued for three days. The reaction was quenched by the addition of water, and extracted with ethyl acetate. This solution was washed with water, dried (MgSO4), and concentrated in vacuo to give the title compound as a yellow oil (4.7 g, 9.7 mmol, 95%); δH [2H6]DMSO 6.52 (1H,d), 6.38 (1H, d), 3.96 (6H,s), 0.77-1.63 (30H,m).

후처리

  1. additionwas added
  2. temperatureto warm to 0° C. for 20 min.
  3. customrecooled to −78° C
  4. stirringstirring
  5. waitwas continued at −78° C. for 15min
  6. temperatureto warm gradually to room temperature
  7. stirringstirring
  8. waitcontinued for three days
  9. customThe reaction was quenched by the addition of water
  10. extractionextracted with ethyl acetate
  11. washThis solution was washed with water
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a29cc88cd380461597e0de6dbb8d2086
출처 데이터셋
uspto-grants-2004_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06723726B1

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