Hydrochloric Acid → 17-Hydroxyprogesterone

HRID 1164192

Reaktionsgleichung

Reaktionsgleichung von HRID 1164192
[C:1]([C@:3]1([OH:23])[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([CH2:20][CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[C:12](=[CH:13][C:14](=[O:22])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)#[CH:2].Cl.C[OH:26]>C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[OH:23][C@:3]1([C@:4]2([CH3:5])[C@H:6]([C@H:9]3[C@H:19]([CH2:20][CH2:21]2)[C@:17]2([CH3:18])[C:12](=[CH:13][C:14](=[O:22])[CH2:15][CH2:16]2)[CH2:11][CH2:10]3)[CH2:7][CH2:8]1)[C:1](=[O:26])[CH3:2]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 5284557Ethisterone

Produkt 1

HCID 623817-Hydroxyprogesterone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 15337Mercuric acetateKatalysator

Versuchsvorschrift

Starting from 3.12 g (0.01 mole) of 17α-ethynyl-17β-hydroxy-androst-4-en-3-one one proceeds as described in Example 9 but after the reaction with mercury(II)-acetate the mixture is not poured onto water but the mixture of 24 ml of concentrated hydrochloric acid and 40 ml of methyl alcohol is added thereto. The reaction mixture is stirred at a temperature of 48° to 50° C. for 8 hours, then it is poured onto water. The separated product is filtered, washed with water and dried. Thus 2.70 g of 17α-hydroxy-pregn-4-ene-3,20-dione are obtained (82.1% of the theoretical yield). The crude product is crystallized from methyl alcohol. Melting point: 212° to 217° C.; [α]D20 =+89° (CHCl3, c=1%).

Aufarbeitung

  1. additionis not poured onto water
  2. additionis added
  3. additionit is poured onto water
  4. filtrationThe separated product is filtered
  5. washwashed with water
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d061a729c62d42ddb4cf0d5da968e04c
Quelldatensatz
uspto-grants-1983_01
Patentnummer
US04368160

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