تفاعل #310879

ord-f37be0df142242e684134c215aeee1c9

معادلة التفاعل

OCCO
Ethylene glycol
Cc1ccc(S(=O)(=O)O)cc1
p-TSA
C[C@]12CCC(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(C)O
17β-hydroxy-17α-methyl-5α-androstan-3-one
→
C[C@]12CCC3(C[C@@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(C)O)OCCO3
title compound
C[C@]12CCC3(C[C@@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(C)O)OCCO3
17β-Hydroxy-17α-methyl-5α-androstan-3-one 3-ethylene ketal

المتفاعلات

OCCO
Ethylene glycol
Cc1ccc(S(=O)(=O)O)cc1
p-TSA
C[C@]12CCC(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(C)O
17β-hydroxy-17α-methyl-5α-androstan-3-one

الكواشف

لا شيء

المذيبات

ClCCl
methylene chloride
ClCCl
methylene chloride

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىis removed
  2. 2
    أخرىThe remainder of the methylene chloride is removed on a rotary evaporator
  3. 3
    درجة الحرارةThe mixture is cooled
  4. 4
    workup.ADDITIONa small amount of a sodium bicarbonate solution and water are added
  5. 5
    ترشيحthe mixture filtered
  6. 6
    غسيلThe filtered solids are washed
  7. 7
    أخرىdried

الإجراء التجريبي

Ethylene glycol (20 ml.) and p-TSA (5 mg.) is added to 17β-hydroxy-17α-methyl-5α-androstan-3-one (sold by Steraloids, Inc., Wilton, N.H., 3.0 g.) in methylene chloride (20 ml.). The mixture is heated on a steam bath until most of the methylene chloride is removed. The remainder of the methylene chloride is removed on a rotary evaporator. The mixture is cooled and a small amount of a sodium bicarbonate solution and water are added and the mixture filtered. The filtered solids are washed and dried to give the title compound, NMR (CDCl3), 0.83, 0.84, 1.20 and 3.29δ.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US04356175uspto-grants-1982_10