تفاعل #502085

ord-1845d7038c7d4ac7a5d33fed45637898

معادلة التفاعل

[O]=[Cr](=[O])([O-])[Cl].c1cc[nH+]cc1
pyridinium chlorochromate
O=[Si]([O-])[O-].[Mg+2]
florisil
C=C(C)[C@@H]1CC[C@]2(CO)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12
betulin
CC(=O)[O-].[Na+]
sodium acetate
→
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
المردود 75.0%

المتفاعلات

[O]=[Cr](=[O])([O-])[Cl].c1cc[nH+]cc1
pyridinium chlorochromate
—
4A
O=[Si]([O-])[O-].[Mg+2]
florisil
C=C(C)[C@@H]1CC[C@]2(CO)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12
betulin
CC(=O)[O-].[Na+]
sodium acetate

الكواشف

لا شيء

المذيبات

ClCCl
CH2Cl2

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.ADDITIONTo a suspension
  2. 2
    ترشيحfiltered through a short column of silica gel
  3. 3
    أخرىThe filtrate is evaporated in vacuo

الإجراء التجريبي

To a suspension of freshly activated powdered 4A molecular sieves (1.2 g), celite (1.2 g), florisil (1.2 g), sodium acetate (500 mg) and pyridinium chlorochromate (1.2 g) in CH2Cl2 (25 mL) add betulin (500 mg). The mixture is to be stirred for 2 hrs, and then filtered through a short column of silica gel. The filtrate is evaporated in vacuo. The residue is then subjected to column chromatography to afford betulone aldehyde (370 mg) as white solid.

المصدر

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