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

HRID 839758노트

반응식

HRID 839758 반응식
[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]

참가 물질

3

반응물 2

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

생성물 1

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

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-4fa104b4f9f845d68230a826d14986e6
출처 데이터셋
uspto-grants-1978_06
특허 번호
US04096253

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