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

HRID 1105739노트

반응식

HRID 1105739 반응식
[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]

참가 물질

5

반응물 3

HCID 7842Propargyl bromideHCID 26110Camphor, oximeHCID 5360545Sodium

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

4.6 g (0.2 mole) of metallic sodium are dissolved in 200 ml of methanol, and 33.4 g (0.2 mole) 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 mole) 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.

후처리

  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

출처 및 근거

ORD 기록
ord-31ba1d9b56c24c278401acfbe1f230e5
출처 데이터셋
uspto-grants-1982_01
특허 번호
US04310348

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