Thioglycolic Acid → 11beta-Hydroxyandrost-4-ene-3,17-dione

HRID 2285878

反応式

HRID 2285878 の反応式
Br[C@:2]12[C@@H:19]([OH:20])[CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH2:14][C:15]3=[O:21])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:23])[CH2:4][CH2:5][C:6](=[O:22])[CH:7]=1.C(O)(=O)CS>C1COCC1.O>[OH:20][C@H:19]1[CH2:18][C@@:16]2([CH3:17])[C@@H:12]([CH2:13][CH2:14][C:15]2=[O:21])[C@H:11]2[C@H:2]1[C@:3]1([CH3:23])[C:8]([CH2:9][CH2:10]2)=[CH:7][C:6](=[O:22])[CH2:5][CH2:4]1

参加物

5

反応物 2

HCID 1133Thioglycolic AcidHCID 111326859alpha-Bromo-11beta-hydroxy-4-androstene-3,17-dione

生成物 1

HCID 9414111beta-Hydroxyandrost-4-ene-3,17-dione収率 87%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 9α-bromo-11β-hydroxyandrost-4-ene-3,17-dione (III, 2.00 g), thioglycolic acid (2.0 ml) in THF (20 ml) and water (5 ml) is stirred under nitrogen at 20°-25°. A chromous sulfate solution (1.4 M, 5.5 ml) is added and the two-phase system is stirred. After four hours, another 4.5 ml of chromous sulfate solution is added and the mixture stirred overnight. The mixture is diluted with water and extracted with ethyl acetate. The ethyl acetate extracts are washed with water, a diluted sodium hydroxide solution, water and saline. The organic phase is dried over sodium sulfate and concentratd to a solid. The solid is crystallized from benzene-hexane to give a first crop of crystals of the title compound (1.38 g, 83.5% chemical yield) which are measured to be 99% pure as measured by GLC and is identical to an authentic sample.

後処理

  1. stirringthe mixture stirred overnight
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate extracts are washed with water
  4. dry with materialThe organic phase is dried over sodium sulfate and concentratd to a solid
  5. customThe solid is crystallized from benzene-hexane

出典と根拠

ORDレコード
ord-6a9a5c473abc47e3bb54b8863a6f6350
出典データセット
uspto-grants-1982_04
特許番号
US04325881

関連ノート

読み込み中…