Water → Testosterone alpha-methylcaprate

Temperature

-10 °C

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).

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

ORD record

ord-78600d75d0e944ef81edb81a0cc71b06

Source dataset

uspto-grants-1980_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04220599