Propargyl bromide → HCID 20541535, compound

HRID 848898Notes

Reaction equation

HRID 848898 reaction equation
[Mg].[CH2:2](Br)[C:3]#[CH:4].[CH3:6][Si:7]([C:10]#[C:11][C:12]([CH2:14][CH2:15][CH2:16][Cl:17])=[O:13])([CH3:9])[CH3:8]>CCOCC>[Cl:17][CH2:16][CH2:15][CH2:14][C:12]([OH:13])([C:11]#[C:10][Si:7]([CH3:8])([CH3:9])[CH3:6])[CH2:4][C:3]#[CH:2]

Participants

5

Reactant 3

HCID 7842Propargyl bromide2×HCID 5462224MagnesiumHCID 20541536HCID 20541536, compound

Product 1

HCID 20541535HCID 20541535, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred suspension of 1.29 grams of magnesium and 10 mg. of mercuric chloride in 12 ml. of ether is added 0.4 ml. of propargyl bromide. The reaction is initiated after stirring at room temperature for a few minutes. The solution of 11.2 grams of 3-chloropropyl trimethylsilylethynyl ketone and 3.51 ml. of propargyl bromide in 13 ml. of ether is added dropwise so that the mixture is very gently boiled during a period of about 40 minutes. After addition is complete, the cooling bath is removed and the mixture is stirred at room temperature for about 1.5 hours. The mixture is recooled in an ice bath and 10 ml. of saturated ammonium chloride solution is added. The resulting white mixture is filtered through diatomaceous earth. The clear mother liquor is washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent is evaporated to dryness giving a red liquid. The liquid is Kugelrohr-distilled to afford the pale yellow liquid distillate which is the desired product.

Workup

  1. additionAfter addition
  2. customthe cooling bath is removed
  3. stirringthe mixture is stirred at room temperature for about 1.5 hours
  4. customThe mixture is recooled in an ice bath
  5. additionof saturated ammonium chloride solution is added
  6. filtrationThe resulting white mixture is filtered through diatomaceous earth
  7. washThe clear mother liquor is washed with saturated sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent is evaporated to dryness
  10. customgiving a red liquid
  11. distillationThe liquid is Kugelrohr-distilled
  12. customto afford the pale yellow liquid distillate which

Sources & evidence

ORD record
ord-e23225890f4c44b1b08dcedfcc5e1ac8
Source dataset
uspto-grants-1981_10
Patent number
US04297516

Reaction notes

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