1-(Dimethylamino)-1-octen-3-one → 3-(Dimethylamino)dec-1-YN-5-one

HRID 971929Notes

Reaction equation

HRID 971929 reaction equation
[CH3:1][N:2]([CH3:12])[CH:3]=[CH:4][C:5](=[O:11])[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C-]#[C-].[Li+].[Li+].[CH2:17]=[CH:18]N>O1CCOCC1>[CH3:12][N:2]([CH3:1])[CH:3]([CH2:4][C:5](=[O:11])[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[C:17]#[CH:18]

Participants

4

Reactant 2

HCID 545630821-(Dimethylamino)-1-octen-3-oneHCID 178464377HCID 178464377, compound

Product 1

HCID 213126353-(Dimethylamino)dec-1-YN-5-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1-(dimethylamino)-1-octen-3-one (4.0 g), described in Example 37, and lithiumacetylide-ethyleneamine (4.0 g) in dry dioxane (25 ml) is stirred at room temperature for 45 min. The mixture is added to ice. The mixture is extracted with ether. The extract is dried (Na2SO4) and then evaporated. The residue is distilled to afford the title compound, b.p. 80°-85° C.

Workup

  1. additionThe mixture is added to ice
  2. extractionThe mixture is extracted with ether
  3. dry with materialThe extract is dried (Na2SO4)
  4. customevaporated
  5. distillationThe residue is distilled

Sources & evidence

ORD record
ord-d33def2ec10e4f3d91063b6b9eedba80
Source dataset
uspto-grants-1979_07
Patent number
US04161608

Reaction notes

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