Propargyl bromide → 7-Chloro-4-hydroxy-4-methyl-1-heptyne

HRID 126703

Reaction equation

HRID 126703 reaction equation
[Mg].BrC(Br)C.[CH2:6](Br)[C:7]#[CH:8].Cl[CH2:11][CH2:12][CH2:13][C:14](=[O:16])[CH3:15].[Cl-:17].[NH4+]>CCOCC>[Cl:17][CH2:6][CH2:7][CH2:8][C:14]([OH:16])([CH3:15])[CH2:13][C:12]#[CH:11]

Participants

7

Reactant 5

HCID 7842Propargyl bromide2×HCID 112011,1-DibromoethaneHCID 25517Ammonium ChlorideHCID 799932-Pentanone, 5-chloro-HCID 5462224Magnesium

Product 1

HCID 128987397-Chloro-4-hydroxy-4-methyl-1-heptyne

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
-5 °C

Procedure

To a mixture of 6.69 g. of magnesium in 20 ml. of ether under argon, is added 0.1 g. of mercuric chloride and 0.1 g. of dibromoethane. The mixture is stirred for 10 minutes and 0.5 ml. of propargyl bromide is added. A 50 ml. portion of ether is added, followed by a solution of 30 g. of 5-chloro-2-pentanone and 32.55 g. of propargyl bromide in 45 ml. of ether with stirring, at a rate to maintain vigorous reflux. The mixture is stirred an additional 15 minutes, cooled to -5° C. and an ice cold saturated solution of ammonium chloride is added dropwise. The ether layer is decanted and filtered. The solids are washed with ether which is also filtered. The combined ether filtrates are washed with water, dried over magnesium sulfate and the solvent removed giving the product as an orange oil.

Workup

  1. additionTo a mixture of 6.69 g
  2. temperatureto maintain vigorous reflux
  3. stirringThe mixture is stirred an additional 15 minutes
  4. customThe ether layer is decanted
  5. filtrationfiltered
  6. washThe solids are washed with ether which
  7. filtrationis also filtered
  8. washThe combined ether filtrates are washed with water
  9. dry with materialdried over magnesium sulfate
  10. customthe solvent removed

Sources & evidence

ORD record
ord-6df25f8fcda442fa8959ab015a89da1c
Source dataset
uspto-grants-1981_03
Patent number
US04254036

Linked notes

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