Propargyl bromide → HCID 12786185, compound

HRID 903382Notes

Reaction equation

HRID 903382 reaction equation
[Mg].[CH2:2](Br)[C:3]#[CH:4].[Cl:6][CH2:7][C:8](=[O:13])[CH2:9][CH2:10][CH2:11][CH3:12].[Cl-].[NH4+]>CCOCC>[Cl:6][CH2:7][C:8]([OH:13])([CH2:9][CH2:10][CH2:11][CH3:12])[CH2:4][C:3]#[CH:2]

Participants

6

Reactant 4

HCID 7842Propargyl bromide2×HCID 25517Ammonium ChlorideHCID 2665711-chlorohexan-2-oneHCID 5462224Magnesium

Product 1

HCID 12786185HCID 12786185, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred suspension of 2.1 g. of magnesium and 20 mg. of mercuric chloride in 25 ml. of ether is added 0.8 ml. of propargyl bromide. After a few minutes of vigorous stirring, to this is added a mixture of 10.75 g. of 1-chloro-2-hexanone and 7.2 ml. of propargyl bromide in 25 ml. of ether, at such a rate that the reaction mixture is maintained at 25°-28° C. After addition, the mixture is stirred at room temperature one hour, cooled in a ice-water bath and 30 ml. of saturated ammonium chloride is added dropwise. The mixture is filtered through celite and washed with ether. The ether solution is concentrated to give 11.0 g. of a yellow liquid which is vacuum distilled to give 6.9 g. of product as a colorless liquid at b.p. 60°-61° C./4 mm.; PMR δ 3.62 (ABq, CH2Cl), 2.53 (d, J=3, C≡C--CH2), 2.06 (t, J=3, HC≡C).

Workup

  1. additionTo a stirred suspension of 2.1 g
  2. waitAfter a few minutes of vigorous stirring
  3. additionto this is added
  4. additiona mixture of 10.75 g
  5. additionAfter addition
  6. temperaturecooled in a ice-water bath
  7. filtrationThe mixture is filtered through celite
  8. washwashed with ether
  9. concentrationThe ether solution is concentrated
  10. customto give 11.0 g
  11. distillationdistilled
  12. customto give 6.9 g

Sources & evidence

ORD record
ord-082fe41ccfff4fb9b876aeeb99aed9f1
Source dataset
uspto-grants-1980_10
Patent number
US04227011

Reaction notes

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