3,4-dihydro-2H-pyran → 3beta-(2-Tetrahydropyranoxy)androst-5-ene-7,17-dione

HRID 551839Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 551839
[CH3:1][C@@:2]12[C:10](=[O:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[C:12]([CH:14]=[C:15]3[CH2:20][C@@H:19]([OH:21])[CH2:18][CH2:17][C@:16]3([CH3:22])[C@H:5]1[CH2:4][CH2:3]2)=[O:13].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[O:40]1[CH:45]=[CH:44][CH2:43][CH2:42][CH2:41]1>>[O:40]1[CH2:45][CH2:44][CH2:43][CH2:42][CH:41]1[O:21][C@H:19]1[CH2:18][CH2:17][C@@:16]2([CH3:22])[C:15](=[CH:14][C:12](=[O:13])[C@@H:6]3[C@@H:5]2[CH2:4][CH2:3][C@@:2]2([CH3:1])[C@H:7]3[CH2:8][CH2:9][C:10]2=[O:11])[CH2:20]1

Komponenten

4

Edukt 3

HCID 80803,4-dihydro-2H-pyranHCID 1933137-Keto-dehydroepiandrosteroneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Produkt 1

HCID 697363133beta-(2-Tetrahydropyranoxy)androst-5-ene-7,17-dione

Versuchsvorschrift

3β-hydroxyandrost-5-ene-7,17-dione (2) (0.5 g, 1.65 mmol) was placed in a dried, argon-flushed flask where it was dissolved in dry dichloromethane (20.0 mL). Pyridinium toluene-p-sulfonate (0.043 g. 0.17 mmol) was added followed by 3,4-dihydro-2H-pyran (0.23 mL, 2.5 mmol) and the solution was stirred at room temperature, under an atmosphere of argon, for 2-3 h. The reaction was quenched by adding water and the product was extracted thrice with ether (3×20 mL). The combined ether extracts were washed with dilute acetic acid, water and bicarbonate solution and dried (MgSO4). Solvent was removed and the crude product was purified using chromatography on silica gel (ethyl acetate-hexane, 15:85, v/v). The compound first eluted was identified as androsta-3,5-diene-7,17-dione (0.150 g), m.p. 167-8° C.

Aufarbeitung

  1. customflushed flask where it
  2. dissolutionwas dissolved in dry dichloromethane (20.0 mL)
  3. customThe reaction was quenched
  4. additionby adding water
  5. extractionthe product was extracted thrice with ether (3×20 mL)
  6. washThe combined ether extracts were washed with dilute acetic acid, water and bicarbonate solution
  7. dry with materialdried (MgSO4)
  8. customSolvent was removed
  9. customthe crude product was purified
  10. washThe compound first eluted

Quellen und Nachweise

ORD-Eintrag
ord-963224c3229448e38d54c7f58113781d
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947846B2

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