2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Exemestane

HRID 1383021

반응식

HRID 1383021 반응식
[CH2:1]=[C:2]1[C:19]2[C@:14]([CH3:21])([CH2:15][CH2:16][C:17](=[O:20])[CH:18]=2)[C@@H:13]2[C@H:4]([C@H:5]3[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:22])[CH2:7][CH2:6]3)[CH2:3]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[CH2:1]=[C:2]1[C:19]2[C@:14]([CH3:21])([CH:15]=[CH:16][C:17](=[O:20])[CH:18]=2)[C@@H:13]2[C@H:4]([C@H:5]3[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:22])[CH2:7][CH2:6]3)[CH2:3]1

참가 물질

4

반응물 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 129518006-Methylideneandrost-4-ene-3,17-dione

생성물 1

HCID 60198Exemestane수율 50.3%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

0.50 g of 6-methylenandrost-4-ene-3,17-dione and 0.57 g of dichlorodicyanobenzoquinone were refluxed in 20 ml of anhydrous dioxane for about 15 hours. To remove the DDQ the suspension was filtered through alumina. After evaporation of the solvent the residue was dissolved in ethyl acetate, the organic layer washed with water, dried over sodium sulfate and the solent removed under vacuum. The crude product was chromatographed on silica gel using hexane/ethyl acetate 40% to yield 0.25 g of pure 6-methylenandrosta-1,4-diene-3,17-dione, m.p. 188°-191° C., λmax 247 mμ (ε13.750). Found: C 81.01, H 8.05. C20H24O2 requires: C 81.04, H 8.16.

후처리

  1. customTo remove the DDQ the suspension
  2. filtrationwas filtered through alumina
  3. customAfter evaporation of the solvent the residue
  4. dissolutionwas dissolved in ethyl acetate
  5. washthe organic layer washed with water
  6. dry with materialdried over sodium sulfate
  7. customthe solent removed under vacuum
  8. customThe crude product was chromatographed on silica gel

출처 및 근거

ORD 기록
ord-4e238f561f2d4149b3487001592a2348
출처 데이터셋
uspto-grants-1989_02
특허 번호
US04808616

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