Propargyl bromide → Propargyl 6-phenylhexanoate

HRID 1654273Notes

Reaction equation

HRID 1654273 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[C:5]1([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O>[C:5]1([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:3][C:2]#[CH:1])=[O:17])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 796956-Phenylhexanoic Acid

Product 1

HCID 15790142Propargyl 6-phenylhexanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Two milliliters of a dry N,N-dimethylformamide solution of 618 mg of propargyl bromide is added by drops to a mixture of 1 g of 6-phenylhexanoic acid, 862 mg of potassium carbonate and 20 ml of dry N,N-dimethylformamide at room temperature with stirring. After stirring for 24 hours, the resultant solution is poured into an aqueous saturated ammonium chloride solution cooled with ice. The resulting mixture is then extracted twice with diethyl ether. The extracts are combined, washed with water and then with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue is subjected to chromatography on silica gel to obtain propargyl 6-phenylhexanoate.

Workup

  1. stirringAfter stirring for 24 hours
  2. temperaturecooled with ice
  3. extractionThe resulting mixture is then extracted twice with diethyl ether
  4. washwashed with water
  5. dry with materialwith an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bbde34a4bb5842ad81577eb5bae35929
Source dataset
uspto-grants-1995_04
Patent number
US05405989

Reaction notes

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