Water → Testosterone alpha-methylcaprate

HRID 866343Notes

Reaction equation

[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]

Participants

Conditions

Temperature: -10 °C

Procedure

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-methylcaprate in the form of an oil with [α]D20 = +77.0° (in methylenechloride) and εmol 16.800 (λmax 240 mμ).

Workup

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

Sources & evidence

ORD record: ord-3bbb499dcdcc4337bb627fa95ef94668
Source dataset: uspto-grants-1978_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04098802

Reaction notes

Loading…