Ozone → (+/-)-cis-4-(2-Oxoethyl)-1,5-dioxaspiro[5.5]undecane-2-acetonitrile

HRID 360020

반응식

HRID 360020 반응식
[CH2:1]([C@H:4]1[O:9][C:8]2([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[O:7][C@@H:6]([CH2:15][C:16]#[N:17])[CH2:5]1)[CH:2]=C.[O:18]=[O+][O-]>ClCCl>[O:18]=[CH:2][CH2:1][C@H:4]1[O:9][C:8]2([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[O:7][C@@H:6]([CH2:15][C:16]#[N:17])[CH2:5]1

참가 물질

4

반응물 2

HCID 24823Ozone2회HCID 15045136(+/-)-cis-4-(2-Propenyl)-1,5-dioxaspiro[5.5]undecane-2-acetonitrile

생성물 1

HCID 86744692(+/-)-cis-4-(2-Oxoethyl)-1,5-dioxaspiro[5.5]undecane-2-acetonitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of (±)-cis-4-(2-propenyl)-1,5-dioxaspiro[5.5]undecane-2-acetonitrile 4.26 9 (19.42 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, 5.6 g (21.36 mmol), is added and the colorless solution is allowed to warm to room temperature. Flash chromatography provides after concentration in vacuo 4.04 g of pure (±)-cis-4-(2-oxoethyl)-1,5-dioxaspiro[5.5undecane-2-acetonitrile.

후처리

  1. customoxygen bubbled through until the blue color
  2. additionTriphenylphosphine, 5.6 g (21.36 mmol), is added
  3. customFlash chromatography provides
  4. concentrationafter concentration in vacuo 4.04 g of pure (±)-cis-4-(2-oxoethyl)-1,5-dioxaspiro[5.5undecane-2-acetonitrile

출처 및 근거

ORD 기록
ord-e112971d4a1845e0b13ba59c2f2a54ef
출처 데이터셋
uspto-grants-1991_03
특허 번호
US05003080

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