Water → 9-Dehydroandrostenedione

HRID 1087672

Reaktionsgleichung

Reaktionsgleichung von HRID 1087672
O[C@:2]12[CH2:19][CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH2:14][C:15]3=[O:20])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:22])[CH2:4][CH2:5][C:6](=[O:21])[CH:7]=1.ClS(O)(=O)=O.O.CCCCCCC>C(Cl)Cl>[CH3:17][C@:16]12[CH2:18][CH:19]=[C:2]3[C@@H:11]([CH2:10][CH2:9][C:8]4[C@:3]3([CH3:22])[CH2:4][CH2:5][C:6](=[O:21])[CH:7]=4)[C@@H:12]1[CH2:13][CH2:14][C:15]2=[O:20]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8900HeptaneHCID 24638Chlorosulfonic acidHCID 104250179alpha-Hydroxyandrost-4-ene-3,17-dione

Produkt 1

HCID 2395959-Dehydroandrostenedione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

9α-Hydroxyandrostenedione (5.00 g.) is dissolved in methylene chloride (50 ml.) and cooled to 0°-5°. A solution of chlorosulfonic acid (2.5 ml.) in methylene chloride (10 ml.) is added slowly over a period of 4 minutes. At the end of the addition TLC shows the reaction is completed. Water (60 ml.) is added to the reaction mixture keeping the temperature at 3°-15°. The mixture is stirred for 2 minutes and heptane (135 ml.) is added. The organic phase is separated and washed twice with water (30 ml. each time). The organic phase is concentrated with heat to about 30 ml. with crystals forming as the solution cools. The mixture is cooled to 0°-5°, filtered, washed with a minimum amount of heptane, and dried at 70° to give androsta-4,9(11)-diene-3,17-dione; 4.45 g. (89.0% weight yield, 94.7% chemical yield), m.p., 195.5°-202°; [α]D +220° (chloroform); UV (methanol) λmax =240 nm (ε=16,300).

Aufarbeitung

  1. temperaturecooled to 0°-5°
  2. customat 3°-15°
  3. customThe organic phase is separated
  4. washwashed twice with water (30 ml
  5. concentrationThe organic phase is concentrated
  6. temperaturewith heat to about 30 ml
  7. customwith crystals forming as the solution cools
  8. temperatureThe mixture is cooled to 0°-5°
  9. filtrationfiltered
  10. washwashed with a minimum amount of heptane
  11. customdried at 70°

Quellen und Nachweise

ORD-Eintrag
ord-833163a22a864aeb9e9397e1b01d537d
Quelldatensatz
uspto-grants-1990_10
Patentnummer
USRE033364

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