Acetone → 1-Acetoxy-3-methoxyestra-1,3,5(10)-trien-17-one

HRID 839758ノート

反応式

HRID 839758 の反応式
[C:1]([O:4][C:5]1[C:22]2[C@@H:21]3[C@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C:16](=[O:23])[CH2:15][CH2:14]4)[CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([OH:24])[CH:6]=1)(=[O:3])[CH3:2].[CH3:25]C(C)=O>>[C:1]([O:4][C:5]1[C:22]2[C@@H:21]3[C@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C:16](=[O:23])[CH2:15][CH2:14]4)[CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([O:24][CH3:25])[CH:6]=1)(=[O:3])[CH3:2]

参加物

3

反応物 2

HCID 180AcetoneHCID 540214941-Acetoxy-3-hydroxyestra-1,3,5(10)-trien-17-one

生成物 1

HCID 544622991-Acetoxy-3-methoxyestra-1,3,5(10)-trien-17-one

実験手順

1-Acetoxy-3-hydroxyestra-1,3,5(10)-trien-17-one (7.6 g, 23 mM) is added to 600 ml of anhydrous acetone in a 3-neck, 1 liter round bottom flask equipped with condenser, magnetic stirring bar, drying tube and pressure-compensated addition funnel. Dimethyl sulfate (3.2 g, 25 mM) is added and the resulting suspension is refluxed for 16 hrs, and then filtered while still warm. The filter cake is washed repeatedly with anhydrous acetone, and the combined filtrates are evaporated in vacuo. The residue is recrystallized from acetone-water to obtain 1-acetoxy-3-methoxyestra-1,3,5(10)-trien-17-one, yield 6.2 g (80%), m.p. 144°-145°. Further recrystallization from CH2Cl2 -hexane gives material of m.p. 150°-151°.

後処理

  1. customequipped with condenser, magnetic stirring bar
  2. customdrying tube and pressure-compensated addition funnel
  3. additionDimethyl sulfate (3.2 g, 25 mM) is added
  4. temperaturethe resulting suspension is refluxed for 16 hrs
  5. filtrationfiltered
  6. temperaturewhile still warm
  7. washThe filter cake is washed repeatedly with anhydrous acetone
  8. customthe combined filtrates are evaporated in vacuo
  9. customThe residue is recrystallized from acetone-water

出典と根拠

ORDレコード
ord-4fa104b4f9f845d68230a826d14986e6
出典データセット
uspto-grants-1978_06
特許番号
US04096253

反応ノート

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