Sodium Acetate → HCID 178460137, compound

HRID 649441Notes

Reaction equation

HRID 649441 reaction equation
[C:1]([CH:5]1[C:10](=[O:11])[CH2:9][CH:8]([CH:12]2[CH2:17][CH:16]3[CH2:18][CH:14]([C:15]3([CH3:20])[CH3:19])[CH:13]2[CH3:21])[CH2:7][C:6]1=[O:22])(=O)[CH2:2][CH3:3].[Cl-].[CH2:24]([O:27][NH3+:28])[CH:25]=[CH2:26].C([O-])(=O)C.[Na+]>C(O)C>[CH2:24]([O:27][NH:28][C:1](=[C:5]1[C:10](=[O:11])[CH2:9][CH:8]([CH:12]2[CH2:17][CH:16]3[CH2:18][CH:14]([C:15]3([CH3:19])[CH3:20])[CH:13]2[CH3:21])[CH2:7][C:6]1=[O:22])[CH2:2][CH3:3])[CH:25]=[CH2:26]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 13589694HCID 13589694, compoundHCID 20141322HCID 20141322, compound

Product 1

HCID 178460137HCID 178460137, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7.5 parts by weight of 2-propionyl-5-(2,6,6-trimethylbicyclo[3.1.1]-hept-3-yl)-cyclohexane-1,3-dione, 2.9 parts per weight of allyloxyammonium chloride, 2.2 parts by weight of anhydrous sodium acetate and 80 of ethanol were stirred at room temperature for 12 hours, the solvent was distilled off under reduced pressure, the residue was stirred with 120 parts of water and 100 parts of methylene chloride, the organic phase was separated off, the aqueous phase was extracted with 50 parts of methylene chloride, and the combined organic phases were washed with water, dried over sodium sulfate and evaporated down under reduced pressure. 2-(1-allyloxyaminopropylidene)-5-(2,6,6-trimethylbicyclo[3.1.1]hept-3-yl)cyclohexane-1,3-dione was obtained in 91% yield as an oil (compound no. 2); nD33 : 1.5317.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. customthe organic phase was separated off
  3. extractionthe aqueous phase was extracted with 50 parts of methylene chloride
  4. washthe combined organic phases were washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated down under reduced pressure

Sources & evidence

ORD record
ord-6028a5f8f7de421d916d4751d1cfcd0e
Source dataset
uspto-grants-1988_04
Patent number
US04740237

Reaction notes

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