Water → 9-Dehydro-progesterone

HRID 1613983ノート

反応式

HRID 1613983 の反応式
O[C@:2]12[CH2:21][CH2:20][C@@:19]3([CH3:22])[C@@H:12]([CH2:13][CH2:14][C@@H:15]3[C:16](=[O:18])[CH3:17])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:24])[CH2:4][CH2:5][C:6](=[O:23])[CH:7]=1.O.C(OCC)(=O)C>S(=O)(=O)(O)O>[CH3:17][C:16](=[O:18])[C@@H:15]1[C@:19]2([CH3:22])[C@H:12]([C@H:11]3[C:2](=[CH:21][CH2:20]2)[C@:3]2([CH3:24])[C:8](=[CH:7][C:6](=[O:23])[CH2:5][CH2:4]2)[CH2:9][CH2:10]3)[CH2:13][CH2:14]1

参加物

5

反応物 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 131887039-Hydroxypregn-4-ene-3,20-dione

生成物 1

HCID 119661839-Dehydro-progesterone

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

実験手順

A solution of 9α-hydroxypregn-4-ene-3,20-dione (218 mg) in 70% (v/v) aqueous sulfuric acid was stirred at room temperature for 1 hour after which the reaction mixture was added dropwise to a stirred mixture of water (5 ml) and ethyl acetate (5 ml). The organic layer was washed with a 5% aqueous potassium carbonate solution, then with water to neutral pH, dried (MgSO4) and concentrated under reduced pressure. The crude product (149 mg), still containing some starting material, was purified by chromatography (silica gel, toluene/acetone 3/1) to afford the title compound.

後処理

  1. washThe organic layer was washed with a 5% aqueous potassium carbonate solution
  2. dry with materialwith water to neutral pH, dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. additionThe crude product (149 mg), still containing some starting material
  5. customwas purified by chromatography (silica gel, toluene/acetone 3/1)

出典と根拠

ORDレコード
ord-4cc3b43d08f445d69d3c11291a104113
出典データセット
uspto-grants-1993_03
特許番号
US05194602

反応ノート

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