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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 1936769
ノート
印刷プレビュー

反応式

HRID 1936769 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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, 12.32 mmol) 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 15 min. 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).

後処理

  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 15 min
  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

出典と根拠

ORDレコード
ord-40c77d69a46b4663a103a98fb074cc33
出典データセット
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06391874B1

反応ノート

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