تفاعل #527907

ord-b6cfd10e4ae540c99c4d52767e53deb8

معادلة التفاعل

CCOC(CO[C@H]1CC[C@@]2(C)C(CC[C@@H]3[C@@H]2CC[C@]2(C)C4OCCOC4C[C@@H]32)C1)OCC
3β-(2,2-diethoxyethoxy)-17-ethylenedioxy-androstane
O=C(O)C(O)C(O)C(=O)O
tartaric acid
O
water
→
C[C@]12CC[C@H](OCC=O)CC1CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3β-formylmethoxy-androstan-17-one
المردود 84.7%

المتفاعلات

—
saturated solution
CCOC(CO[C@H]1CC[C@@]2(C)C(CC[C@@H]3[C@@H]2CC[C@]2(C)C4OCCOC4C[C@@H]32)C1)OCC
3β-(2,2-diethoxyethoxy)-17-ethylenedioxy-androstane
O=C(O)C(O)C(O)C(=O)O
tartaric acid
O
water

الكواشف

لا شيء

المذيبات

C1COCCO1
dioxane

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.ADDITIONwere then added
  2. 2
    استخلاصthe residue was extracted with methylene chloride
  3. 3
    غسيلThe organic layer was washed with water
  4. 4
    تجفيفdried over anhydrous sodium sulfate
  5. 5
    أخرىevaporated to dryness under reduced pressure
  6. 6
    أخرىThe crude product was purified by flash-chromatography (SiO2)

الإجراء التجريبي

A solution of 7.2 g of 3β-(2,2-diethoxyethoxy)-17-ethylenedioxy-androstane, in 250 ml of dioxane and 250 ml of a saturated solution of tartaric acid was heated at 70° C. for 2 hrs in a nitrogen atmosphere, 100 ml of water were then added and the residue was extracted with methylene chloride. The organic layer was washed with water, dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The crude product was purified by flash-chromatography (SiO2) using as eluant n-hexane/ethyl acetate 70/30 to give 4.5 g of 3β-formylmethoxy-androstan-17-one as a white solid.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05521167uspto-grants-1996_05