Pyridine → HCID 46935131, compound

HRID 1486597Notes

Reaction equation

HRID 1486597 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[C:12](Cl)(=[O:22])/[CH:13]=[CH:14]/[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C(O)(=O)/C=C/CCCCCCC.S(Cl)(Cl)=O>O1CCCC1>[C:12]([N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)(=[O:22])/[CH:13]=[CH:14]/[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

7

Reactant 5

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 31268PyrrolidineHCID 5282724trans-2-Decenoic acidHCID 11206263HCID 11206263, compound

Product 1

HCID 46935131HCID 46935131, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A tetrahydrofuran solution (20 mL) of pyrrolidine (0.71 g, 0.01 mol) containing pyridine (0.79 g, 0.01 mol) was added to a tetrahydrofuran solution (20 mL) of (E)-2-decenoic acid chloride (1.9 g, 0.01 mol), synthesized using (E)-2-decenoic acid and thionyl chloride, and the mixture was heated under refluxing in a warm water bath for 3 hours. After distilling off excess tetrahydrofuran, water was added to a liquid reaction mixture, and the liquid mixture was extracted with ethyl acetate, and washed with water, and ethyl acetate was distilled off. The residue was purified with silica gel column chromatography (developing solvent:hexane:ethyl acetate=1:3), to give an intended compound (1.4 g) in the form of a colorless oily substance.

Workup

  1. customsynthesized
  2. temperaturethe mixture was heated
  3. temperatureunder refluxing in a warm water bath for 3 hours
  4. distillationAfter distilling off excess tetrahydrofuran, water
  5. additionwas added to a liquid reaction mixture
  6. extractionthe liquid mixture was extracted with ethyl acetate
  7. washwashed with water, and ethyl acetate
  8. distillationwas distilled off
  9. customThe residue was purified with silica gel column chromatography (developing solvent:hexane:ethyl acetate=1:3)

Sources & evidence

ORD record
ord-32497ed8a7904fc6b92eec59bd80723f
Source dataset
uspto-grants-2016_08
Patent number
US09428477B2

Reaction notes

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