Propargyl bromide → (2Z)-1,7,7-trimethyl-N-(prop-2-yn-1-yloxy)bicyclo[2.2.1]heptan-2-imine

HRID 1389408ノート

反応式

HRID 1389408 の反応式
[Na].[CH3:2][C:3]12[C:9]([CH3:11])([CH3:10])[CH:6]([CH2:7][CH2:8]1)[CH2:5][C:4]2=[N:12][OH:13].[CH2:14](Br)[C:15]#[CH:16]>CO>[CH2:16]([O:13][N:12]=[C:4]1[CH2:5][CH:6]2[C:9]([CH3:10])([CH3:11])[C:3]1([CH3:2])[CH2:8][CH2:7]2)[C:15]#[CH:14]

参加物

5

反応物 3

HCID 7842Propargyl bromideHCID 26110Camphor, oximeHCID 5360545Sodium

生成物 1

HCID 52692(2Z)-1,7,7-trimethyl-N-(prop-2-yn-1-yloxy)bicyclo[2.2.1]heptan-2-imine収率 81%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

4.6 g (0.2 moles) of metallic sodium are dissolved in 200 ml of methanol, and 33.4 g (0.2 moles) of (±)-1,7,7-trimethyl-bicyclo[2,2,1]heptane-2-one-oxime are added to the solution. After one hour of boiling 23.8 g (0.2 moles) of propargyl bromide are introduced, and the reaction is continued for a further hour. The mixture is cooled, the separated sodium bromide is filtered off, the filtrate is concentrated, and the concentrate is subjected to fractional distillation in vacuo. 33.2 g (81%) of (±)-2-(propargyloxyimino)-1,7,7-trimethyl-bicyclo[2,2,1]heptane are obtained as a light yellow oil; b.p.: 94° C./1.5 mm Hg, nD20 =1.4955.

後処理

  1. waitthe reaction is continued for a further hour
  2. temperatureThe mixture is cooled
  3. filtrationthe separated sodium bromide is filtered off
  4. concentrationthe filtrate is concentrated
  5. distillationthe concentrate is subjected to fractional distillation in vacuo

出典と根拠

ORDレコード
ord-b639f6dc1b3044a8833c16a1689a1b41
出典データセット
uspto-grants-1981_01
特許番号
US04244888

反応ノート

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