Acetic Acid → 7alpha-Methylestr-4-ene-3,11,17-trione

HRID 637618

반응식

HRID 637618 반응식
[OH:1][C@@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C@@H:4]1[C:9]([CH2:10][C@H:11]2[CH3:21])=[CH:8][C:7](=[O:22])[CH2:6][CH2:5]1.C(O)(=O)C.S(=O)(=O)(O)O.C>O.C(OCC)(=O)C.C(Cl)Cl.O.S([O-])([O-])(=O)=O.[Mn+2].[O-2].[O-2].[O-2].[Cr+6]>[CH3:21][C@@H:11]1[CH2:10][C:9]2[C@H:4]([CH2:5][CH2:6][C:7](=[O:22])[CH:8]=2)[C@@H:3]2[C@@H:12]1[C@H:13]1[C@@:17]([CH2:19][C:2]2=[O:1])([CH3:18])[C:16](=[O:20])[CH2:15][CH2:14]1

참가 물질

10

반응물 4

HCID 176Acetic AcidHCID 297MethaneHCID 1118Sulfuric AcidHCID 1202027311alpha-Hydroxy-7alpha-methylestr-4-ene-3,17-dione

생성물 1

HCID 572776857alpha-Methylestr-4-ene-3,11,17-trione

시약·촉매·용매 5

HCID 962Water촉매HCID 177577Manganese sulfate monohydrate촉매HCID 10219390chromium (VI) trioxide촉매2회HCID 962Water용매3회HCID 21226138Dichloromethane ethylacetate용매

실험 절차

A mixture of 11α-hydroxy-7α-methylestr-4-ene-3,17-dione (A, obtained from Fermentation) and acetic acid (7.5 ml) is stirred and cooled to about 10° in a cold water bath. The following reagents are added: water (6 drops), manganese sulfate monohydrate (0.1 g) in water (1 ml), chromium trioxide (0.66 g) in water (2 ml), and concentrated sulfuric acid (0.6 ml). The chromium trioxide solution is added over a 15 minute period. After 1/2 hour water (10 ml) is added and the crystals of the product are collected, washed with water and dried to give a solid. The solid is dissolved in hot ethyl acetate/methylene chloride (1/1) and decolorized with a little charcoal and silica gel and then filtered through celite. The appropriate fractions are pooled and concentrated to give crystals, UV (ethyl alcohol) λmax =239 nm (ε=16250); IR (mull) 1740, 1707, 1672 and 1616; MS (m/e)=300, 282, 272, and 258.

후처리

  1. temperaturecooled to about 10° in a cold water bath
  2. additionThe following reagents are added
  3. customthe crystals of the product are collected
  4. washwashed with water
  5. customdried
  6. customto give a solid
  7. filtrationfiltered through celite
  8. concentrationconcentrated
  9. customto give crystals, UV (ethyl alcohol) λmax =239 nm (ε=16250)

출처 및 근거

ORD 기록
ord-ef76c2cfb25c45848d5eb8ad055c7b8e
출처 데이터셋
uspto-grants-1985_12
특허 번호
US04557867

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