臭氧 → (+/-)-cis-6-(2-Oxoethyl)-1,3-dioxane-4-acetonitrile

HRID 5703

反应方程式

HRID 5703 反应方程式
[CH2:1]([C@H:4]1[O:9][CH2:8][O:7][C@@H:6]([CH2:10][C:11]#[N:12])[CH2:5]1)[CH:2]=C.[O:13]=[O+][O-]>ClCCl>[O:13]=[CH:2][CH2:1][C@H:4]1[O:9][CH2:8][O:7][C@@H:6]([CH2:10][C:11]#[N:12])[CH2:5]1

参与物

4

反应物 2

HCID 24823臭氧2 次HCID 67833318(+/-)-cis-6-(2-Propenyl)-1,3-dioxane-4-acetonitrile

产物 1

HCID 86744693(+/-)-cis-6-(2-Oxoethyl)-1,3-dioxane-4-acetonitrile

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂

实验过程

A solution of (±)-cis-6-(2-propenyl)-1,3-dioxane-4-acetonitrile, 2.57 g (15.36 mmol), in 100 mL of dichloromethane is cooled to -78° C. under nitrogen. Ozone (Welsback generator, flow rate 0.1, voltage=90V) is then passed through a fritted gas inlet tube into the solution until the blue color of ozone appears. The current is turned off, and oxygen bubbled through until the blue color is discharged. Triphenylphosphine, 4,87 g (28.58 mmol), is added and the colorless solution is allowed to warm to room temperature. Flash chromatography provides after concentration in vacuo 2.3 g of pure (±)-cis-6-(2-oxoethyl)-1,3-dioxane-4-acetonitrile.

后处理

  1. customoxygen bubbled through until the blue color
  2. additionTriphenylphosphine, 4,87 g (28.58 mmol), is added
  3. customFlash chromatography provides
  4. concentrationafter concentration in vacuo 2.3 g of pure (±)-cis-6-(2-oxoethyl)-1,3-dioxane-4-acetonitrile

来源与证据

ORD记录
ord-fd5a9b495e42491992d07ec5b729edec
来源数据集
uspto-grants-1993_09
专利号
US05245047

关联笔记

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