1,2-Dibromoethane → 4-Hydroxy-4-methyl-oct-1-yn-7-ene

HRID 1732460Notes

Reaction equation

HRID 1732460 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 205650044-Hydroxy-4-methyl-oct-1-yn-7-ene

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
  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-5c0bb03e4b2c4159ae2293bf16e8f5e4
Source dataset
uspto-grants-1980_12
Patent number
US04237307

Reaction notes

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