Artemisinic Acid → Artemisinic alcohol

HRID 1698525Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1698525
[CH3:1][C@H:2]1[C@@H:7]2[CH2:8][CH2:9][C:10]([CH3:12])=[CH:11][C@@H:6]2[C@H:5]([C:13]([C:15](O)=[O:16])=[CH2:14])[CH2:4][CH2:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][C@H:2]1[C@@H:7]2[CH2:8][CH2:9][C:10]([CH3:12])=[CH:11][C@@H:6]2[C@H:5]([C:13]([CH2:15][OH:16])=[CH2:14])[CH2:4][CH2:3]1

Komponenten

4

Edukt 2

HCID 10922465Artemisinic AcidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 15983960Artemisinic alcoholAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Artemisinic acid (100.0 mg, 0.43 mmol) was dissolved in THF (10.0 mL) and LiAlH4 (17.0 mg, 0.45 mmol) was added. The heterogeneous mixture was held at reflux (70° C.) for 15 h. After cooling, the reaction was quenched with water (3.0 mL) and 15% aqueous NaOH (3.0 mL), stirred for 10 min and filtered through celite. The organic phase was separated, dried over MgSO4, and concentrated using a rotary evaporator. The product was purified by column chromatography (2:1 hexanes/EtOAc) to give 61.0 mg (65% yield) of the alcohol as a colorless oil. A minor amount of artemisinic acid contaminant was further removed by column chromatography over neutral alumina (Brockman activity 1). Characterization data was consistent with literature values.

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe reaction was quenched with water (3.0 mL) and 15% aqueous NaOH (3.0 mL)
  3. filtrationfiltered through celite
  4. customThe organic phase was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customa rotary evaporator
  8. customThe product was purified by column chromatography (2:1 hexanes/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-6254e5c8d90a4d288e5150408fc67d73
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163980B2

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