反応 #502086

ord-ae05c6e12d1f40a1be49aa744b0431b9

反応方程式

C=C(C)[C@@H]1CC[C@]2(C=O)CC[C@]3(C)[C@@H](CC[C@@H]4[C@@]5(C)C=CC(=O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12
betulone aldehyde
OO
H2O2
[Na+].[O-][Cl+][O-]
NaClO2
→
C=C(C)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12
betulonic acid

反応物

C=C(C)[C@@H]1CC[C@]2(C=O)CC[C@]3(C)[C@@H](CC[C@@H]4[C@@]5(C)C=CC(=O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12
betulone aldehyde
OO
H2O2
[Na+].[O-][Cl+][O-]
NaClO2

試薬

なし

溶媒

O
water
—
NaH2PO4.H2O
CC#N.O
CH3CN—H2O

反応条件

温度
2.5°CELSIUS
詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    温度the mixture warmed to room temperature
  2. 2
    その他The reaction is quenched by addition of Na2S2O5 (380 mg)
  3. 3
    抽出extracted with ethyl acetate
  4. 4
    抽出The organic extract
  5. 5
    洗浄is washed with water and brine
  6. 6
    乾燥dried (Na2SO4)
  7. 7
    ろ過filtered
  8. 8
    濃縮concentrated

実験手順

The betulone aldehyde prepared from the last step is dissolved in a mixture of NaH2PO4.H2O (877 mg) and CH3CN—H2O (17 mL) and the suspension cooled to 0-5° C. 30% aqueous H2O2 (220 μL) and a solution of NaClO2 (200 mg) in water (16 mL) are then successively added, the mixture warmed to room temperature and stirred at this temperature for 1 h. The reaction is quenched by addition of Na2S2O5 (380 mg), and extracted with ethyl acetate. The organic extract is washed with water and brine, dried (Na2SO4), filtered, and concentrated. The residue is then subjected to column chromatography to afford betulonic acid (550 mg) as white solid.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US08088757B2uspto-grants-2012_01