1,2-Dibromoethane → HCID 20565004, compound

HRID 126727Notes

Reaction equation

HRID 126727 reaction equation
[Mg].Br[CH2:3][CH2:4]Br.[CH2:6](Br)C#C.[O:10]=[C:11]([CH3:16])[CH2:12][CH2:13][CH:14]=[CH2:15].[Cl-].[NH4+]>CCOCC>[OH:10][C:11]([CH3:6])([CH2:12][CH2:13][CH:14]=[CH2:15])[CH2:16][C:3]#[CH:4]

Participants

7

Reactant 5

HCID 78391,2-DibromoethaneHCID 7842Propargyl bromide2×HCID 79895-Hexene-2-oneHCID 25517Ammonium ChlorideHCID 5462224Magnesium

Product 1

HCID 20565004HCID 20565004, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A mixture of 19.45 g. of magnesium, 0.15 g. of mercuric chloride and 0.5 ml. of 1,2-dibromoethane in 40 ml. of ether, under argon, is stirred for 5 minutes. A 0.5 ml. portion of propargylbromide is added followed by 160 ml. of ether. To the stirred mixture is added dropwise a solution of 60.0 g. of 5-oxo-1-hexene and 87.3 g. of propargyl bromide in 100 ml. of ether, at such a rate as to maintain a vigorous reflux. After addition is complete, the mixture is stirred for 20 minutes, cooled in an ice-bath and a saturated solution of ammonium chloride is added dropwise. The solid is removed by filtration through Celite and washing with ether. The solvent is removed from the filtrate giving the product as an orange liquid.

Workup

  1. additionA mixture of 19.45 g
  2. additionTo the stirred mixture is added dropwise a solution of 60.0 g
  3. additionAfter addition
  4. temperaturecooled in an ice-bath
  5. customThe solid is removed by filtration through Celite
  6. washwashing with ether
  7. customThe solvent is removed from the filtrate

Sources & evidence

ORD record
ord-de79c9b864c7407ba4069d6dced46f0a
Source dataset
uspto-grants-1981_03
Patent number
US04254036

Reaction notes

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