Acetic Acid → Npc182939

HRID 1085934Notes

Reaction equation

HRID 1085934 reaction equation
[CH3:1][C@H:2]1[C@@H:12]2[CH2:13][CH2:14][C@@:15]3([CH3:19])[O:17][O:18][C@:11]42[C@H:5]([C@@H:6]([CH3:20])[C:7]([O:9][C@@H:10]4[O:16]3)=[O:8])[CH2:4][CH2:3]1.[BH4-].[Na+].C(O)(=O)C>CO>[CH3:1][C@H:2]1[C@@H:12]2[CH2:13][CH2:14][C:15]3([CH3:19])[O:17][O:18][C@:11]42[C@H:5]([C@@H:6]([CH3:20])[C@@H:7]([OH:8])[O:9][C@@H:10]4[O:16]3)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 68827ArtemisininHCID 4311764Sodium borohydride

Product 1

HCID 456410Npc182939

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4 g (0.014 m) of qinghaosu (I) in 200 ml of methanol, was added 4 g of sodium borohydride in small portions, keeping the reaction mixture at 0°-5°. After stirring for 60 min, the mixture was neutralized with glacial acetic acid, concentrated and diluted with water. The white precipitate formed was collected and dried. Recrystallization of the solid from acetone-hexane afforded white needles mp: 153°-58° C., 3.2 g (80).

Workup

  1. customat 0°-5°
  2. concentrationconcentrated
  3. additiondiluted with water
  4. customThe white precipitate formed
  5. customwas collected
  6. customdried
  7. customRecrystallization of the solid from acetone-hexane afforded white needles mp: 153°-58° C., 3.2 g (80)

Sources & evidence

ORD record
ord-2dde5313947f46a090dca57632cbefff
Source dataset
uspto-grants-1991_04
Patent number
US05011951

Reaction notes

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