Hydrogen Peroxide → HCID 14433155, compound

HRID 2363895Notes

Reaction equation

HRID 2363895 reaction equation
[CH3:1][C@H:2]1[C@@H:11]2[CH2:12][CH2:13][C@:14]3([CH3:18])[O:16][O:17][C@:10]42[C@H:5]([C:6]([CH3:19])=[CH:7][O:8][C@@H:9]4[O:15]3)[CH2:4][CH2:3]1.C1COCC1.O.[OH-].[K+].OO>C1COCC1>[CH3:1][C@H:2]1[C@@H:11]2[CH2:12][CH2:13][C@:14]3([CH3:18])[O:16][O:17][C@:10]42[C@H:5]([C@@H:6]([CH3:19])[CH2:7][O:8][C@@H:9]4[O:15]3)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14797Potassium HydroxideHCID 11054607HCID 11054607, compoundHCID 21881883Oxolane--water (1/1)

Product 1

HCID 14433155HCID 14433155, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of anhydrodihydroartemisinin (AHA) (2.08 g, 7.8 mmol) in THF (20 ml), was dropwise added a solution of BH3/THF complex in THF soln. (1 M; 14 ml) with ice-cooling. After being stirred at room temperature for 1 h, the mixture was treated with THF-water (1:1; 4 ml), followed by a mixture of aq. KOH (10%; 10 ml) and aq. H2O2 (50%; 4 ml).

Workup

  1. temperature(1 M; 14 ml) with ice-cooling

Sources & evidence

ORD record
ord-cf02062b29d242b9a343b150eba32342
Source dataset
uspto-grants-2014_04
Patent number
US08692003B2

Reaction notes

Loading…