p-Toluenesulfonic acid → 7alpha-Methylestr-5-ene-3,11,17-trione

HRID 637619노트

반응식

HRID 637619 반응식
[CH3:1][C@@H:2]1[CH2:19][C:18]2[C@H:13]([CH2:14][CH2:15][C:16](=[O:20])[CH:17]=2)[C@@H:12]2[C@@H:3]1[C@H:4]1[C@@:8]([CH2:10][C:11]2=[O:21])([CH3:9])[C:7](=[O:22])[CH2:6][CH2:5]1.C(Cl)Cl.C(OC(OCC)OCC)C.CC1C=CC(S(O)(=O)=O)=CC=1>C(O)CO>[CH3:1][C@@H:2]1[CH:19]=[C:18]2[C@H:13]([CH2:14][CH2:15][C:16](=[O:20])[CH2:17]2)[C@@H:12]2[C@@H:3]1[C@H:4]1[C@@:8]([CH2:10][C:11]2=[O:21])([CH3:9])[C:7](=[O:22])[CH2:6][CH2:5]1

참가 물질

6

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 6344DichloromethaneHCID 31214Ethyl orthoformateHCID 572776857alpha-Methylestr-4-ene-3,11,17-trione

생성물 1

HCID 571664657alpha-Methylestr-5-ene-3,11,17-trione

시약·촉매·용매 1

HCID 174Ethylene Glycol용매

실험 절차

A mixture of 7α-methylestr-4-ene-3,11,17-trione (B, Example 23, 4.1 g), methylene chloride (50 ml), ethylene glycol (31 ml), triethylorthoformate (14 ml) and p-TSA (41 mg) are refluxed for 3 hours. The mixture is then cooled and washed with bicarbonate and water, then dried to a solid. NMR shows a mixture of Δ5 (10) and Δ5 isomers. The product is used without further purification.

후처리

  1. temperatureare refluxed for 3 hours
  2. temperatureThe mixture is then cooled
  3. washwashed with bicarbonate and water
  4. customdried to a solid
  5. additiona mixture of Δ5 (10) and Δ5 isomers
  6. customThe product is used without further purification

출처 및 근거

ORD 기록
ord-78e658e710aa4e7dac150b4cd35bb2f7
출처 데이터셋
uspto-grants-1985_12
특허 번호
US04557867

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