Pyridine → HCID 15790146, compound

HRID 1654271Notes

Reaction equation

HRID 1654271 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](Cl)=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([OH:20])C#C.N1C=C[CH:24]=[CH:23][CH:22]=1>C1(C)C=CC=CC=1>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:15][CH2:22][C:23]#[CH:24])=[O:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7859Propargyl alcoholHCID 15790145HCID 15790145, compound

Product 1

HCID 15790146HCID 15790146, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

542 Milligrams of 8-phenyloctanoyl chloride was added by drops to a mixture of 140 mg of propargyl alcohol, 198 mg of pyridine and 20 ml of dry toluene with stirring and ice-cooling. After dropwise addition, the resultant solution was stirred for additional 12 hours at room temperature. The thus stirred solution was then poured into ice water. The toluene layer was separated from the resulting mixture. The aqueous layer was extracted once with toluene. These toluene layers were combined, washed with water and then with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off from the dried layer under reduced pressure. The resulting residue was subjected to chromatography on silica gel to obtain 530 mg of propargyl 8-phenyloctanoate.

Workup

  1. temperatureice-cooling
  2. additionAfter dropwise addition
  3. customThe toluene layer was separated from the resulting mixture
  4. extractionThe aqueous layer was extracted once with toluene
  5. washwashed with water
  6. dry with materialwith an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off from the dried layer under reduced pressure

Sources & evidence

ORD record
ord-c566e28ef38345acaef253697bfeddaf
Source dataset
uspto-grants-1995_04
Patent number
US05405989

Reaction notes

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