Water → 4-piperidino-3-[3-[3-(2-methylthioethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one

HRID 639739Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 639739
[C:1]([C:4]1[C:5](=[O:12])[O:6][C:7]([CH3:11])=[CH:8][C:9]=1O)(=[O:3])[CH3:2].[CH3:13][S:14][CH2:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH:21]=O.[NH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.O>C(Cl)(Cl)Cl>[N:26]1([C:9]2[CH:8]=[C:7]([CH3:11])[O:6][C:5](=[O:12])[C:4]=2[C:1](=[O:3])[CH:2]=[CH:21][C:20]2[CH:23]=[CH:24][CH:25]=[C:18]([O:17][CH2:16][CH2:15][S:14][CH3:13])[CH:19]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8082PiperidineHCID 231317123-(2-Methylthioethoxy)benzaldehydeHCID 546784943-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one

Produkt 1

HCID 686767284-piperidino-3-[3-[3-(2-methylthioethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-oneAusbeute 6,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

In 8 ml of chloroform were dissolved 85.7 mg of 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one, 100 mg of 3-(2-methylthioethoxy)benzaldehyde and 30.3 mg of piperidine, and the solution was heated under refluxing for 13 hours while water was removed with a Soxhlet's extractor filled with a molecular sieve. After cooling to room temperature, the reaction mixture washed successively with 10% hydrochloric acid and an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated. Precipitated crystals were filtered, and this was subjected to silica gel column chromatography to obtain 10.1 mg of 4-piperidino-3-[3-[3-(2-methylthioethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one [Compound No. (14b)] as a pale yellow crystal.

Aufarbeitung

  1. temperaturethe solution was heated
  2. customwas removed with a Soxhlet's extractor
  3. additionfilled with a molecular sieve
  4. washthe reaction mixture washed successively with 10% hydrochloric acid
  5. dry with materialan aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customPrecipitated crystals
  8. filtrationwere filtered

Quellen und Nachweise

ORD-Eintrag
ord-934c1954b5144109b3eb6659a3e30f33
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691883B2

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