Water → Testosterone alpha-methylcaprate

HRID 25953

反応式

HRID 25953 の反応式
[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]

参加物

6

反応物 3

HCID 962WaterHCID 6013TestosteroneHCID 20300744HCID 20300744、化合物

生成物 1

HCID 86735824Testosterone alpha-methylcaprate

試薬・触媒・溶媒 2

HCID 180Acetone溶媒2 回HCID 1049Pyridine溶媒2 回

反応条件

温度
-10 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2de783d56c79468a88c22f506f86963d
出典データセット
uspto-grants-1979_04
特許番号
US04147783

関連ノート

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