Benzene → Dihydroartemisinin ethyl ether

HRID 1699474

Reaction equation

HRID 1699474 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@@H:6]([CH3:20])[C@@H:7]([OH:19])[O:8][C@@H:9]4[O:15]3)[CH2:4][CH2:3]1.Cl[Si](C)(C)C.[CH:26]1C=CC=C[CH:27]=1>>[CH3:26][CH2:27][O:19][C@H:7]1[O:8][C@@H:9]2[O:15][C:14]3([CH3:18])[O:16][O:17][C@@:10]42[C@@H:5]([CH2:4][CH2:3][C@@H:2]([CH3:1])[C@@H:11]4[CH2:12][CH2:13]3)[C@H:6]1[CH3:20]

Participants

4

Reactant 3

HCID 241BenzeneHCID 6397ChlorotrimethylsilaneHCID 456410Npc182939

Product 1

HCID 72416Dihydroartemisinin ethyl ether

Procedure

Another method is reported by Bhakuni et al. (Bhakuni R. S; Jain D. C and Sharma, R P., Indian J. Chemistry, 34B, 529-30 (1995). Arteether was prepared by dissolving dihydroartemisinin in alcohol and benzene mixture and then adding chlorotrimethylsilane as acid catalyst. The reaction was stirred for 2 hrs. at room temperature. The reaction mixture was washed with 10% sodium acetate solution and workup as usual method. The other products formed during the reaction were removed by column chromatography, to obtain pure arteether.

Workup

  1. customArteether was prepared
  2. customat room temperature
  3. washThe reaction mixture was washed with 10% sodium acetate solution and workup as usual method
  4. customThe other products formed during the reaction
  5. customwere removed by column chromatography

Sources & evidence

ORD record
ord-5cf77ee2a02043f39f01a2ebca8217db
Source dataset
uspto-grants-2002_02
Patent number
US06346631B1

Linked notes

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