Hydrochloric Acid → 13-Ethyl-17beta-(2-dimethylaminoethoxy)-3-methoxygona-1,3,5(10)-triene

HRID 1077248

Reaktionsgleichung

Reaktionsgleichung von HRID 1077248
[NH2-].[Na+].[CH2:3]([C@:5]12[CH2:13][CH2:12][C@@H:11]3[C:14]4[CH:15]=[CH:16][C:17]([O:22][CH3:23])=[CH:18][C:19]=4[CH2:20][CH2:21][C@H:10]3[C@@H:9]1[CH2:8][CH2:7][C@@H:6]2[OH:24])[CH3:4].Cl.[CH3:26][N:27]([CH2:29][CH2:30]Cl)[CH3:28].Cl>C1C=CC=CC=1>[CH2:3]([C@:5]12[CH2:13][CH2:12][C@@H:11]3[C:14]4[CH:15]=[CH:16][C:17]([O:22][CH3:23])=[CH:18][C:19]=4[CH2:20][CH2:21][C@H:10]3[C@@H:9]1[CH2:8][CH2:7][C@@H:6]2[O:24][CH2:30][CH2:29][N:27]([CH3:28])[CH3:26])[CH3:4]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 24533Sodium amideHCID 66432(17beta)-13-Ethyl-3-methoxygona-1,3,5(10)-trien-17-olHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Produkt 1

HCID 6814316313-Ethyl-17beta-(2-dimethylaminoethoxy)-3-methoxygona-1,3,5(10)-triene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel2×

Versuchsvorschrift

Stir a solution of 860 mg. of sodium amide in 15 ml. of benzene and add 3.0 g. of dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17β-ol in 15 ml. of benzene. Heat for 2 hours at 70°-83°. Cool to room temperature and add 1.58 g. of N,N-dimethylamino-2-chloroethane hydrochloride and reflux for 16 hours. Pour over ice and acidify reaction mixture with 2 N hydrochloric acid. Extract with ether and basify the aqueous layer with 15% sodium hydroxide. Isolate material with ether. Evaporate the ether to obtain dl-13-ethyl-17β-(2-dimethylaminoethoxy)-3-methoxygona-1,3,5(10)-triene.

Aufarbeitung

  1. temperatureHeat for 2 hours at 70°-83°
  2. additionadd 1.58 g
  3. extractionExtract with ether
  4. customEvaporate the ether

Quellen und Nachweise

ORD-Eintrag
ord-804e56982a2a4808889991d28281b950
Quelldatensatz
uspto-grants-1976_05
Patentnummer
US03959322

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