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

HRID 5687

반응식

HRID 5687 반응식
[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

참가 물질

4

반응물 2

HCID 24823Ozone2회HCID 15045109(+/-)-cis-2,2-Dimethyl-6-(2-propenyl)-1,3-dioxane-4-acetonitrile

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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 cooled 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.

후처리

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

출처 및 근거

ORD 기록
ord-b6eb58361dae4facaccd1c29d8d6a8b6
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05245047

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