Dimethyl Sulfate → 1,3-Dimethoxyestra-1,3,5(10)-trien-17-one

HRID 839760노트

반응식

HRID 839760 반응식
[OH:1][C:2]1[C:19]2[C@@H:18]3[C@H:9]([C@H:10]4[C@@:14]([CH2:16][CH2:17]3)([CH3:15])[C:13](=[O:20])[CH2:12][CH2:11]4)[CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([O:21][CH3:22])[CH:3]=1.S(OC)(O[CH3:27])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:27][O:1][C:2]1[C:19]2[C@@H:18]3[C@H:9]([C@H:10]4[C@@:14]([CH2:16][CH2:17]3)([CH3:15])[C:13](=[O:20])[CH2:12][CH2:11]4)[CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([O:21][CH3:22])[CH:3]=1

참가 물질

5

반응물 3

HCID 6497Dimethyl Sulfate2회HCID 11430Potassium CarbonateHCID 545489061-Hydroxy-3-methoxyestra-1,3,5(10)-trien-17-one

생성물 1

HCID 537114841,3-Dimethoxyestra-1,3,5(10)-trien-17-one

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A suspension of 1-hydroxy-3-methoxyestra-1,3,5(10)-trien-17-one (2.5 g, 8.3 mM), dimethyl sulfate (1.3 g, 10.3 mM) and potassium carbonate (1.2 g) in 250 ml of anhydrous acetone is refluxed with vigorous stirring for 6 hrs. An additional 0.5 g of dimethyl sulfate is added and the suspension refluxed for 14 hrs. The reaction mixture is filtered while warm and the solids washed well with acetone. The combined acetone filtrates are evaporated in vacuo and the residue is recrystallized from methanol-H2O. Two recrystallizations give 1,3-dimethoxyestra-1,3,5(10)-trien-17-one, yield 1.91 g (73%); m.p. 132°-133°.

후처리

  1. temperatureis refluxed
  2. temperaturethe suspension refluxed for 14 hrs
  3. filtrationThe reaction mixture is filtered
  4. temperaturewhile warm
  5. washthe solids washed well with acetone
  6. customThe combined acetone filtrates are evaporated in vacuo
  7. customthe residue is recrystallized from methanol-H2O
  8. customTwo recrystallizations

출처 및 근거

ORD 기록
ord-4424f8ccdde842ada0fad0c8f77c8924
출처 데이터셋
uspto-grants-1978_06
특허 번호
US04096253

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