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

HRID 1886267

反応式

HRID 1886267 の反応式
[CH3:1][C:2]1([CH3:14])[O:7][C@@H:6]([CH2:8][C:9]#[N:10])[CH2:5][C@@H:4]([CH2:11][CH:12]=C)[O:3]1.[O:15]=[O+][O-]>ClCCl>[O:15]=[CH:12][CH2:11][C@H:4]1[O:3][C:2]([CH3:14])([CH3:1])[O:7][C@@H:6]([CH2:8][C:9]#[N:10])[CH2:5]1

参加物

4

反応物 2

HCID 24823Ozone2 回HCID 15045109(+/-)-cis-2,2-Dimethyl-6-(2-propenyl)-1,3-dioxane-4-acetonitrile

生成物 1

HCID 86744690(+/-)-cis-6-(2-Oxoethyl)-2,2-dimethyl-1,3-dioxane-4-acetonitrile

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of (±)-cis-2,2-dimethyl-6-(2-propenyl)-1,3-dioxane-4-acetonitrile, 3 g (15.36 mmol), in 100 mL of dichloromethane is cooed to -78° C. under nitrogen. Ozone (Welsbach generator, flow rate 0.1, voltage=90 V) 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, 4.2 g (16 mmol), is added and the colorless solution allowed to warm to room temperature. Flash chromatography provides, after concentration in vacuo, 2.5 g of pure (±)-cis-6-(2-oxoethyl)-2,2-dimethyl-1,3-dioxane-4-acetonitrile.

後処理

  1. customis cooed to -78° C. under nitrogen
  2. customoxygen bubbled through until the blue color
  3. additionTriphenylphosphine, 4.2 g (16 mmol), is added
  4. customFlash chromatography provides
  5. concentrationafter concentration in vacuo, 2.5 g of pure (±)-cis-6-(2-oxoethyl)-2,2-dimethyl-1,3-dioxane-4-acetonitrile

出典と根拠

ORDレコード
ord-117d6c3ad65c49bca7ce033c2098fb15
出典データセット
uspto-grants-1992_09
特許番号
US05149837

関連ノート

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