Propargyl alcohol → Propargyl 6-phenylhexanoate

HRID 1654272Notes

Reaction equation

HRID 1654272 reaction equation
Cl.C(N=C=N[CH2:7][CH2:8][CH2:9]N(C)C)C.[C:13]1([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O)C#C>C(Cl)(Cl)Cl>[C:13]1([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:9][C:8]#[CH:7])=[O:25])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7859Propargyl alcoholHCID 796956-Phenylhexanoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 15790142Propargyl 6-phenylhexanoateYield 26%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Five hundred milligrams of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to a mixture of 500 mg of 6-phenylhexanoic acid and 20 ml of dry chloroform at room temperature with stirring. After the resultant mixture had been stirred for 30 minutes at room temperature, 146 mg of propargyl alcohol was added thereto at room temperature. Thereafter, the resulting mixture was stirred for 12 hours at room temperature, poured into ice water and extracted with chloroform. The chloroform extract was washed with an aqueous saturated ammonium chloride solution and then with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to chromatography on silica gel to obtain 155 mg of propargyl 6-phenylhexanoate.

Workup

  1. customat room temperature
  2. stirringThereafter, the resulting mixture was stirred for 12 hours at room temperature
  3. extractionextracted with chloroform
  4. extractionThe chloroform extract
  5. washwas washed with an aqueous saturated ammonium chloride solution
  6. dry with materialwith an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a273ecb38446452b95ef44ac9c724f2d
Source dataset
uspto-grants-1995_04
Patent number
US05405989

Reaction notes

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