Propargyl bromide → Heptopargil

HRID 1105739Notes

Reaction equation

HRID 1105739 reaction equation
[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]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 26110Camphor oximeHCID 5360545Sodium

Product 1

HCID 52692HeptopargilYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-31ba1d9b56c24c278401acfbe1f230e5
Source dataset
uspto-grants-1982_01
Patent number
US04310348

Reaction notes

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