Propargyl bromide → HCID 20565046, compound

HRID 224512Notes

Reaction equation

HRID 224512 reaction equation
[Mg].Br[CH:3](Br)[CH3:4].[CH2:6](Br)C#C.[CH2:10]=[C:11]([CH2:15][CH2:16][CH3:17])[C:12](=[O:14])[CH3:13].[Cl-].[NH4+]>CCOCC>[OH:14][C:12]([CH3:6])([C:11](=[CH2:10])[CH2:15][CH2:16][CH3:17])[CH2:13][C:3]#[CH:4]

Participants

7

Reactant 5

HCID 7842Propargyl bromide2×HCID 112011,1-DibromoethaneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 12288567HCID 12288567, compound

Product 1

HCID 20565046HCID 20565046, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
0 °C

Procedure

To a mixture of 5.0 g. of magnesium and 100 mg. of mercuric chloride in 10 ml. of ether is added with stirring, one ml. of dibromoethane. The mixture is stirred for 10 minutes and 0.5 ml. of propargyl bromide is added. An additional 50 ml. of ether is added, followed by a solution of 17.5 g. of 3-methylene-2-hexanone and 27.8 g. of propargyl bromide in 60 ml. of ether, dropwise at a rate to maintain vigorous reflux. The mixture is refluxed for 1/2 hour, cooled to 0° C. and saturated ammonium chloride solution is added dropwise. The mixture is filtered through Celite and the solids are washed with ether. The ether solution is dried over magnesium sulfate and the ether is removed giving the desired product.

Workup

  1. additionTo a mixture of 5.0 g
  2. stirringThe mixture is stirred for 10 minutes
  3. temperatureThe mixture is refluxed for 1/2 hour
  4. filtrationThe mixture is filtered through Celite
  5. washthe solids are washed with ether
  6. dry with materialThe ether solution is dried over magnesium sulfate
  7. customthe ether is removed

Sources & evidence

ORD record
ord-d3e5d69c51e843388412c435b94937d6
Source dataset
uspto-grants-1980_11
Patent number
US04232166

Reaction notes

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