تفاعل #502086

ord-ae05c6e12d1f40a1be49aa744b0431b9

معادلة التفاعل

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

المتفاعلات

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

الكواشف

لا شيء

المذيبات

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

ظروف التفاعل

درجة الحرارة
2.5°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةthe mixture warmed to room temperature
  2. 2
    أخرىThe reaction is quenched by addition of Na2S2O5 (380 mg)
  3. 3
    استخلاصextracted with ethyl acetate
  4. 4
    استخلاصThe organic extract
  5. 5
    غسيلis washed with water and brine
  6. 6
    تجفيفdried (Na2SO4)
  7. 7
    ترشيحfiltered
  8. 8
    تركيزconcentrated

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08088757B2uspto-grants-2012_01