AT160275B - Process for the preparation of esters of pregnen- (5) -ol- (3) -one- (20). - Google Patents

Process for the preparation of esters of pregnen- (5) -ol- (3) -one- (20).

Info

Publication number
AT160275B
AT160275B AT160275DA AT160275B AT 160275 B AT160275 B AT 160275B AT 160275D A AT160275D A AT 160275DA AT 160275 B AT160275 B AT 160275B
Authority
AT
Austria
Prior art keywords
pregnen
esters
preparation
residue
acid
Prior art date
Application number
Other languages
German (de)
Original Assignee
Ig Farbenindustrie Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Publication date
Application granted granted Critical
Publication of AT160275B publication Critical patent/AT160275B/en

Links

Description

  

   <Desc/Clms Page number 1> 
 



  Verfahren zur Herstellung von Estern des   Pregnen- (5)-ol- (3)-ons- (20).   



   Es wurde gefunden, dass man Ester des Pregnen-(5)-ol-(3)-ons-(20) in der Weise herstellen kann, wenn man das Nitril oder das Diäthylamid der 3-Acyloxyätiocholen-(5)-säure (österr. Patentschrift Nr. 159222) mit Hilfe einer Grignard-Verbindung in das entsprechende Methylketimin und dieses durch Verseifung in das Methylketon überführt. 
 EMI1.1 
 
 EMI1.2 
 das Gemisch drei Stunden auf dem Wasserbad, dampft das Lösungsmittel ab und erwärmt den Rückstand weitere acht Stunden. Danach wird der Rückstand mit Eiswasser und verdünnter Schwefel- 

 <Desc/Clms Page number 2> 

 
 EMI2.1 
 das man aus   3-Acetoxyätiocholen- (5) -säurechlorid durch Umsetzung   mit Diäthylamin erhält.

   Nach   dreistündigem Erhitzen auf dem Wasserbad   wird   das Lösungsmittel im Vakuum abdestilliert   und der Rückstand weitere zwölf Stunden auf dem Wasserbad erhitzt. Der   Rückstand   wird nun mit Eiswasser und verdünnter Schwefelsäure zersetzt, ausgeäthert und die   ätherische   Lösung mit Säure und Natriumearbonatlösung gewaschen. Nach Abdampfen des Äthers wird der   Rückstand   im Hochvakuum (2000 ;   0'02   mm) destilliert. Nach Umlösen des Destillates aus wässerigem Alkohol wird der Essigsäureester 
 EMI2.2 




   <Desc / Clms Page number 1>
 



  Process for the preparation of esters of pregnen- (5) -ol- (3) -one- (20).



   It has been found that esters of Pregnen- (5) -ol- (3) -one- (20) can be prepared in such a way if one uses the nitrile or the diethylamide of 3-acyloxyätiocholen- (5) -ic acid (Austrian Patent specification No. 159222) with the aid of a Grignard compound into the corresponding methyl ketimine and this converted into the methyl ketone by saponification.
 EMI1.1
 
 EMI1.2
 the mixture on the water bath for three hours, the solvent evaporated and the residue heated for a further eight hours. Then the residue is treated with ice water and dilute sulfur

 <Desc / Clms Page number 2>

 
 EMI2.1
 obtained from 3-Acetoxyätiocholen- (5) acid chloride by reaction with diethylamine.

   After heating on the water bath for three hours, the solvent is distilled off in vacuo and the residue is heated on the water bath for a further twelve hours. The residue is then decomposed with ice water and dilute sulfuric acid, extracted with ether and the ethereal solution washed with acid and sodium carbonate solution. After evaporation of the ether, the residue is distilled in a high vacuum (2000; 0'02 mm). After redissolving the distillate from aqueous alcohol, the acetic acid ester becomes
 EMI2.2

Claims (1)

PATENT-ANSPRUCH : Verfahren zur Herstellung von Estern des Pregnen- (5)-ol- (3)-ons- (20), dadurch gekennzeichnet, dass man das Nitril oder das Diäthylamid der 3-Acyloxyätiocholen-(5)-säure mit Hilfe einer GrignardVerbindung in das entsprechende Methylketimin und dieses durch Verseifung in das Methylketon überführt. PATENT CLAIM: Process for the preparation of esters of pregnen- (5) -ol- (3) -one- (20), characterized in that the nitrile or the diethylamide of 3-acyloxyethiocholenic (5) acid with the help of a Grignard compound is converted into the corresponding methyl ketimine and this converted into the methyl ketone by saponification.
AT160275D 1936-04-11 Process for the preparation of esters of pregnen- (5) -ol- (3) -one- (20). AT160275B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE160275T 1936-04-11

Publications (1)

Publication Number Publication Date
AT160275B true AT160275B (en) 1941-03-25

Family

ID=29413175

Family Applications (1)

Application Number Title Priority Date Filing Date
AT160275D AT160275B (en) 1936-04-11 Process for the preparation of esters of pregnen- (5) -ol- (3) -one- (20).

Country Status (1)

Country Link
AT (1) AT160275B (en)

Similar Documents

Publication Publication Date Title
AT160275B (en) Process for the preparation of esters of pregnen- (5) -ol- (3) -one- (20).
AT112628B (en) Process for the preparation of concentrated acetic acid.
DE459604C (en) Process for the production of concentrated acetic acid
AT159222B (en) Process for the preparation of 3-Oxyätiocholansäure or 3-Oxyätiocholen- (5) -äure or their 3-Acylderivaten.
DE708115C (en) Process for the preparation of 3-epiacetoxyaetioallocholanic acid
AT160403B (en) Process for the preparation of isomer mixtures of estradiol or lower hydrogen analogues thereof or their derivatives.
AT230897B (en) Process for the preparation of the new 1,5-diethyl-5-Δ &lt;1&gt; -cyclo-pentenylbarbituric acid
AT147163B (en) Process for the preparation of organic bismuth compounds.
AT158800B (en) Method of obtaining dihydro-follicular hormone from the urine of pregnant mares.
AT130656B (en) Process for obtaining concentrated formic acid.
DE430770C (en) Process for the preparation of physiologically active substances
DE674753C (en) Process for the preparation of ª ‰ - (p-Oxyphenyl) -isopropylmethylamine
CH200363A (en) Process for the preparation of methacrylic acid amide.
AT158266B (en) Process for the preparation of pregnanol- (3) -one- (20) and allo-pregnanol- (3) -one- (20) or their derivatives.
AT147319B (en) Process for the preparation of acyl derivatives of the octahydrofollicle hormones.
CH242837A (en) Process for the preparation of the new α, α&#39;-dichloroadipic acid chloride.
CH184765A (en) Process for the production of vinyl esters.
CH222904A (en) Process for the preparation of 5-isoamylamino-hexene (1).
CH208443A (en) Process for the preparation of a lipoid-soluble mixture with bactericidal properties.
CH184419A (en) Process for the preparation of a mixture of stereoisomeric dihydrofollicle hormones of the formula C18H24O2.
CH162632A (en) Process for the preparation of 3-ethoxy-4-oxy-benzaldehyde.
CH125473A (en) Process for the preparation of 1-oxo-2-methyl-3-phenyl-propene-2.
CH195775A (en) Process for the preparation of a new ester.
CH141806A (en) Process for the preparation of a therapeutically active substance from the sex glands.
CH122519A (en) Process for the preparation of an aralkylamine.