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

HRID 637618

反応式

HRID 637618 の反応式
[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

参加物

10

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 962Water触媒HCID 177577Manganese sulfate monohydrate触媒HCID 10219390chromium (VI) trioxide触媒2 回HCID 962Water溶媒3 回HCID 21226138Dichloromethane ethylacetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ef76c2cfb25c45848d5eb8ad055c7b8e
出典データセット
uspto-grants-1985_12
特許番号
US04557867

関連ノート

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