Artemisinic Acid → Artemisinic alcohol

HRID 410153Notes

Reaction equation

HRID 410153 reaction equation
[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

Participants

4

Reactant 2

HCID 10922465Artemisinic AcidHCID 21226445Aluminium lithium hydride

Product 1

HCID 15983960Artemisinic alcoholYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-81614717d42248ae9204b99b1d12d943
Source dataset
uspto-grants-2014_06
Patent number
US08759632B2

Reaction notes

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