Acetic Acid → Npc182939

HRID 1085933ノート

反応式

HRID 1085933 の反応式
[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+].CC(O)=O>CO.O>[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

参加物

6

反応物 3

HCID 176Acetic AcidHCID 68827ArtemisininHCID 4311764Sodium borohydride

生成物 1

HCID 456410Npc182939収率 88%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To a stirred solution of qinghaosu (I) (240 g, 0.85 mol) in 12 l MeOH was added NaBH4 (240 g, 6.34 mol) over a period of 2 h keeping the reaction mixture at 0°-5° C. After an additional stirring for 1.30 h under the same conditions, the mixture was neutralized with 375 ml AcOH maintaining the temperature in the range of 0°-5° C. and subsequently diluted with 24 l water. After stirring for 1 h at 0°-1° C., the white precipitate formed was collected and washed with 700 ml water-MeOH (2:1, 0°-5° C.) The filtrate was stirred for 14 h at 0° C. The small amount of material precipitated was collected and washed with H2O--MeOH (2:1, 2×30 ml). The wet crops were combined and dissolved in 7 l CH2Cl2. After drying on magnesium sulphate (120 g) and evaporation of the solvent, 212 g (88%) of (II) was obtained: mp 149°-153° C.

後処理

  1. customat 0°-5° C
  2. customin the range of 0°-5° C.
  3. stirringAfter stirring for 1 h at 0°-1° C.
  4. customthe white precipitate formed
  5. customwas collected
  6. washwashed with 700 ml water-MeOH (2:1, 0°-5° C.) The filtrate
  7. stirringwas stirred for 14 h at 0° C
  8. customThe small amount of material precipitated
  9. customwas collected
  10. washwashed with H2O--MeOH (2:1, 2×30 ml)
  11. dissolutiondissolved in 7 l CH2Cl2
  12. customAfter drying on magnesium sulphate (120 g) and evaporation of the solvent

出典と根拠

ORDレコード
ord-6a664a66efdc48ae976c3e64effbdedd
出典データセット
uspto-grants-1991_04
特許番号
US05011951

反応ノート

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