Ozone → (+/-)-cis-6-(2-Oxoethyl)-1,3-dioxane-4-acetonitrile
反応式
[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]1参加物
4
実験手順
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.
後処理
- customoxygen bubbled through until the blue color
- additionTriphenylphosphine, 4,87 g (28.58 mmol), is added
- customFlash chromatography provides
- concentrationafter concentration in vacuo 2.3 g of pure (±)-cis-6-(2-oxoethyl)-1,3-dioxane-4-acetonitrile
出典と根拠
- ORDレコード
- ord-fd5a9b495e42491992d07ec5b729edec
- 出典データセット
- uspto-grants-1993_09
- 特許番号
- US05245047
反応ノート
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