Acrolein → HCID 20144474, compound

HRID 649011Notes

Reaction equation

HRID 649011 reaction equation
[C:1]([C:4]#[CH:5])([CH3:3])=[CH2:2].C([Li])CCC.[CH:11]([CH:13]=[CH2:14])=[O:12].[NH4+].[Cl-]>CCCCCC.O1CCCC1>[CH3:2][C:1](=[CH2:3])[C:4]#[C:5][CH:11]([OH:12])[CH:13]=[CH2:14]

Participants

7

Reactant 4

HCID 7847AcroleinHCID 25517Ammonium ChlorideHCID 62323IsopropenylacetyleneHCID 178418339Butyllithium

Product 1

HCID 20144474HCID 20144474, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

10 g Isopropenylacetylene are taken up in abs. tetrahydrofuran and under an inert gas 94.5 ml of 1.6M solution of n-butyllithium in hexane added dropwise at -20°. The mixture is then cooled to -78° and 8.5 g of acrolein added dropwise. The reaction mixture is warmed to room temperature, poured into saturated aqueous NH4Cl and repeatedly extracted with ether. The organic phase is washed, dried and concentrated in vacuum. An oil is obtained.

Workup

  1. temperatureThe mixture is then cooled to -78°
  2. extractionrepeatedly extracted with ether
  3. washThe organic phase is washed
  4. customdried
  5. concentrationconcentrated in vacuum
  6. customAn oil is obtained

Sources & evidence

ORD record
ord-0a33d5a5bccb415e8fff42413fad8b60
Source dataset
uspto-grants-1988_04
Patent number
US04737516

Reaction notes

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