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Ethyl Acetate → 16beta-Ethyl-17beta-n-hexanoyloxyacetoxy-4,9(10)-estradien-3-one

HRID 64734
ノート
印刷プレビュー

反応式

HRID 64734 の反応式
[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[OH:22])=[C:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2].[C:23]([O:30][CH2:31][C:32](Cl)=[O:33])(=[O:29])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C(OCC)(=O)C.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[O:22][C:32](=[O:33])[CH2:31][O:30][C:23](=[O:29])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[C:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 12831651HCID 12831651、化合物HCID 147665592-Chloro-2-oxoethyl hexanoate

生成物 1

HCID 1860425916beta-Ethyl-17beta-n-hexanoyloxyacetoxy-4,9(10)-estradien-3-one

試薬・触媒・溶媒 2

HCID 14284
4-(Dimethylamino)pyridine
触媒
HCID 1140Toluene溶媒

反応条件

温度
25 °C

実験手順

In 20 ml of toluene are dissolved 1.5 g of 16β-ethyl-17β-hydroxy-4,9(10)-estradien-3-one and 1.92 g of 4-dimethylaminopyridine, and 1.6 ml of n-hexanoyloxyacetyl chloride is added. The mixture is stirred at 50°-60° C. for 3 hours. After cooling to 25° C., the mixture is poured into a mixture of ethyl acetate (200 ml) and saturated aqueous sodium hydrogen carbonate (50 ml). The organic layer is separated and the aqueous layer is extracted with ethyl acetate. These organic layers are combined, washed with water and saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent is then distilled off under reduced pressure and the residue is chromatographed on a silica gel column. Following passage of diisopropyl ether-n-hexane (1:1), elution is carried out with 1000 ml of a 3:2 mixture of the same solvents. The eluate is evaporated under reduced pressure to remove the solvent, giving 1.69 g of the above-identified compound as a light-yellow viscous oil.

後処理

  1. additionis added
  2. customThe organic layer is separated
  3. extractionthe aqueous layer is extracted with ethyl acetate
  4. washwashed with water and saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent is then distilled off under reduced pressure
  7. customthe residue is chromatographed on a silica gel column
  8. washpassage of diisopropyl ether-n-hexane (1:1), elution
  9. additionis carried out with 1000 ml of a 3:2 mixture of the same solvents
  10. customThe eluate is evaporated under reduced pressure
  11. customto remove the solvent

出典と根拠

ORDレコード
ord-38de621d11e3468f857ce3b881a9a486
出典データセット
uspto-grants-1986_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04609650

反応ノート

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