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

HRID 5703

反応式

HRID 5703 の反応式
[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

反応物 2

HCID 24823Ozone2 回HCID 67833318(+/-)-cis-6-(2-Propenyl)-1,3-dioxane-4-acetonitrile

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

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

  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

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

関連ノート

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