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

HRID 893495

反応式

HRID 893495 の反応式
[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

参加物

4

反応物 2

HCID 24823Ozone2 回HCID 15045136(+/-)-cis-4-(2-Propenyl)-1,5-dioxaspiro[5.5]undecane-2-acetonitrile

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of (±)-cis-4-(2-propenyl)-1,5-dioxa-spiro[5.5]undecane-2-acetonitrile 4.26 g (19.42 mmol), in 100 mL of dichloromethane is cooled to -78° C. under nitrogen. Ozone (Welsbach 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, 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-oxo-ethyl)-1,5-dioxaspiro[5.5]undecane-2-acetonitrile.

後処理

  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-oxo-ethyl)-1,5-dioxaspiro[5.5]undecane-2-acetonitrile

出典と根拠

ORDレコード
ord-a7f1bc57faa84919bf4d4125578e02b5
出典データセット
uspto-grants-1992_06
特許番号
US05124482

関連ノート

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