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

HRID 839760ノート

反応式

HRID 839760 の反応式
[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

参加物

5

反応物 3

HCID 6497Dimethyl Sulfate2 回HCID 11430Potassium CarbonateHCID 545489061-Hydroxy-3-methoxyestra-1,3,5(10)-trien-17-one

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-4424f8ccdde842ada0fad0c8f77c8924
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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