Water → Testosterone alpha-methylcaprate

HRID 25953

Reaktionsgleichung

[CH3:1][C@@:2]12[C@@H:10]([OH:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH2:13][C:14]3[C@@:20]([CH3:21])([C@H:5]1[CH2:4][CH2:3]2)[CH2:19][CH2:18][C:16](=[O:17])[CH:15]=3.CC(=[O:34])C(Cl)CCCCCCCC.O>N1C=CC=CC=1.CC(C)=O>[CH3:1][C@@:2]12[C@@H:10]([OH:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH2:13][C:14]3[C@@:20]([CH3:21])([C@H:5]1[CH2:4][CH2:3]2)[CH2:19][CH2:18][C:16](=[O:17])[CH:15]=3.[CH3:1][CH:2]([CH2:3][CH2:4][CH2:5][CH2:20][CH2:19][CH2:18][CH2:16][CH3:15])[C:10](=[O:34])[O-:11]

Komponenten

Reaktionsbedingungen

Temperatur: -10 °C

Versuchsvorschrift

To a solution of 2 g testosterone in a mixture of 8 ml pyridine and 8 ml acetone, cooled to -10° C., was added dropwise in a nitrogen atmosphere a solution of 4 ml α-methyl-decanoyl-chloride in 12 ml acetone. The mixture was stirred for 16 hours at 0° C., whereafter 4 ml pyridine and 8 ml water were added to the mixture. The mixture was stirred for 1 hour at 0° C. and 2 hours at 45° C. and then poured out in 200 ml ice-water. Extraction with diethylether neutralisation of the extracts, evaporation of the diethylether and chromatography of the residue on silicagel with toluene/ethylacetate 8/2 gave 3.0 g testosterone α-methyl-caprate in the form of an oil with [α]D20 =+77.0° (in methylenechloride) and εmol 16.800 (λmax 240 mμ).

Aufarbeitung

additionwere added to the mixture
extractionExtraction
customwith diethylether neutralisation of the extracts, evaporation of the diethylether and chromatography of the residue on silicagel with toluene/ethylacetate 8/2

Quellen und Nachweise

ORD-Eintrag: ord-2de783d56c79468a88c22f506f86963d
Quelldatensatz: uspto-grants-1979_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04147783

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