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

HRID 1587164

反応式

HRID 1587164 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-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-dioxaspiro5.5]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-oxoethyl)-1,5-dioxaspiro5

出典と根拠

ORDレコード
ord-1371378ee0394323abc4cdd48dc80678
出典データセット
uspto-grants-1993_06
特許番号
US05216174

関連ノート

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