تفاعل #94829

ord-846a8806a8f34412a7df715c710e35fc

معادلة التفاعل

Cl
hydrochloric acid
COC(=CCl)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)C3=CC[C@@]21C
21-Chloro-17α-hydroxy-20-methoxypregna-4,9(11),20-trien-3-one
C1CCOC1
THF
CC(C)=O
acetone
→
C[C@]12CCC(=O)C=C1CC[C@@H]1C2=CC[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CCl
title compound
C[C@]12CCC(=O)C=C1CC[C@@H]1C2=CC[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CCl
21-Chloro-17α-hydroxypregna-4,9(11)-diene-3,20-dione

المتفاعلات

Cl
hydrochloric acid
COC(=CCl)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)C3=CC[C@@]21C
21-Chloro-17α-hydroxy-20-methoxypregna-4,9(11),20-trien-3-one
C1CCOC1
THF
CC(C)=O
acetone

الكواشف

لا شيء

المذيبات

CO
methanol
CCCCCC
hexane

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةthe resulting slurry heated at 40° for 1.5 hours
  2. 2
    درجة الحرارةThe mixture is cooled to 20°-25°
  3. 3
    أخرىThe solids are isolated by filtration
  4. 4
    غسيلwashed with hexane/ethyl acetate (85/15, 13 ml)

الإجراء التجريبي

21-Chloro-17α-hydroxy-20-methoxypregna-4,9(11),20-trien-3-one (VII, Example 4, 1.0 g), THF (4 ml), acetone (4.9 ml), and methanol (1.4 ml) are mixed. Aqueous hydrochloric acid (6 N, 0.44 ml) is added and the resulting slurry heated at 40° for 1.5 hours. The mixture is cooled to 20°-25° and diluted with hexane (3 ml). The solids are isolated by filtration and washed with hexane/ethyl acetate (85/15, 13 ml) to give the title compound.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US04342702uspto-grants-1982_08