Pyridine → HCID 69110769, Verbindung

HRID 349724Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 349724
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[C:14](=[O:19])[CH2:15][CH:16]([OH:18])[CH:17]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].N1C=CC=CC=1.[C:26](OC(=O)C)(=[O:28])[CH3:27]>ClCCl>[C:26]([O:18][CH:16]1[CH2:15][C:14](=[O:19])[C:13]([C:5]2[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:17]1)(=[O:28])[CH3:27]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 691095992-(3,4,5-Trimethoxyphenyl)-4-hydroxy-cyclopent-2-en-1-one

Produkt 1

HCID 69110769HCID 69110769, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 2-(3,4,5-trimethoxyphenyl)-4-hydroxy-cyclopent-2-en-1-one (3 gm, 11.36 mmol) in dichloromethane (30 ml) was cooled to 0° C. using ice-salt bath. To the cold solution dry pyridine (1.70 gm, 1.73 ml; 26.0 mmol) was added and stirred at 0° C. for 10 min. To the stirred solution, acetic anhydride (1.63 gm, 1.50 ml, 16.0 mmol) was added dropwise while maintaining the temperature below 0° C. The reaction mixture was stirred at room temperature for 15 h (monitored by TLC) then quenched by adding cold, dilute hydrochloric acid. The organic layer was washed three times with water, 10% sodium bicarbonate solution and finally brine. The organic layer was dried over sodium sulfate and concentrated to dryness under reduced pressure using a rotary evaporator. The crude residue was purified by column chromatography using silica gel (petroleum ether: acetone as eluent) to collect the pure 4-acetoxy-2-(3,4,5-trimethoxy-phenyl)-cyclopent-2-en-1-one (2.56 gm, 73.47%).

Aufarbeitung

  1. temperaturewhile maintaining the temperature below 0° C
  2. stirringThe reaction mixture was stirred at room temperature for 15 h (monitored by TLC)
  3. customthen quenched
  4. additionby adding cold
  5. washThe organic layer was washed three times with water, 10% sodium bicarbonate solution and finally brine
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated to dryness under reduced pressure
  8. customa rotary evaporator
  9. customThe crude residue was purified by column chromatography
  10. customto collect the pure 4-acetoxy-2-(3,4,5-trimethoxy-phenyl)-cyclopent-2-en-1-one (2.56 gm, 73.47%)

Quellen und Nachweise

ORD-Eintrag
ord-da71b07023ff466faa38bf466943ef6a
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179937B2

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