Acetic Acid → Npc182939

HRID 1085932

反応式

HRID 1085932 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>[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

5

反応物 3

HCID 176Acetic AcidHCID 68827ArtemisininHCID 4311764Sodium borohydride

生成物 1

HCID 456410Npc182939収率 79.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a stirred solution of 240 g (0.85 mol) of qinghaosu (I) in 12 l MeOH was added 240 g (6.34 mol) NaBH4 over a period of 1.75 h, keeping the reaction mixture at 0°-5° C. After an additional stirring for 1.25 h under the same conditions, the mixture was neutralized with 375 ml AcOH maintaining the temperature in the 0°-5° C. range, concentrated by distilling off 8.5 l of solvent (45° C./400 mm), and diluted with 7.5 l cold H2O--MeOH (2:1, 0°-5° C.). The filtrate was stored for 14 h at 4° C. The small amount of precipitate formed was collected and washed with 2×30 ml H2O--MeOH (2:1, 0°-5° C.). The wet crops were pooled and dissolved in 7 l CH2Cl2. After drying (120 g MgSO4) and evaporation of the solvent, 191.4 g (79%) of (II) was obtained: mp 149°-153° C.

後処理

  1. customat 0°-5° C
  2. customin the 0°-5° C. range
  3. concentrationconcentrated
  4. distillationby distilling off 8.5 l of solvent (45° C./400 mm)
  5. additiondiluted with 7.5 l cold H2O--MeOH (2:1, 0°-5° C.)
  6. waitThe filtrate was stored for 14 h at 4° C
  7. customThe small amount of precipitate formed
  8. customwas collected
  9. washwashed with 2×30 ml H2O--MeOH (2:1, 0°-5° C.)
  10. dissolutiondissolved in 7 l CH2Cl2
  11. customAfter drying
  12. custom(120 g MgSO4) and evaporation of the solvent

出典と根拠

ORDレコード
ord-0007e1a2e34f48ddbd0bd33214625179
出典データセット
uspto-grants-1991_04
特許番号
US05011951

関連ノート

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