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

HRID 1659457

反応式

HRID 1659457 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 concentrated 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
  5. concentrationconcentrated to a solid
  6. customThe solid is crystallized from benzene-hexane

出典と根拠

ORDレコード
ord-301131bbee3b46aca2ddd5fdb22772e3
出典データセット
uspto-grants-1981_12
特許番号
US04304727

関連ノート

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