Acetic Acid → 13-Ethyl-3-methoxygona-1,3,5(10),8-tetraen-17beta-ol

HRID 1077162

Reaktionsgleichung

Reaktionsgleichung von HRID 1077162
[CH2:1]([C@:3]12[CH2:11][CH2:10][C:9]3[C:12]4[CH:13]=[CH:14][C:15]([O:20][CH3:21])=[CH:16][C:17]=4[CH2:18][CH2:19][C:8]=3[C@@H:7]1[CH2:6][CH2:5][C:4]2=[O:22])[CH3:2].[BH4-].[Na+].C(O)(=O)C>CO>[CH2:1]([C@:3]12[CH2:11][CH2:10][C:9]3[C:12]4[CH:13]=[CH:14][C:15]([O:20][CH3:21])=[CH:16][C:17]=4[CH2:18][CH2:19][C:8]=3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[OH:22])[CH3:2]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 111113Einecs 227-699-7HCID 4311764Sodium borohydride

Produkt 1

HCID 11130013-Ethyl-3-methoxygona-1,3,5(10),8-tetraen-17beta-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Add 13β-ethyl-3-methoxygona-1,3,5(10),8-tetraen-17-one (16.8 g.) to a solution of sodium borohydride (6 g.) in methanol (500 cc.), swirl the mixture which boils spontaneously. When all the material has been added and the reaction has subsided, add acetic acid (15 cc.). Reduce the mixture in volume by evaporation of most of the solvent, add water and extract the product with ether. Evapoate the washed and dried extracts to obtain crude crystalline product (16.8 g.), m.p. 102°-5° on recrystallization from acetonitrile.

Aufarbeitung

  1. additionWhen all the material has been added
  2. customReduce the mixture in volume by evaporation of most of the solvent
  3. additionadd water
  4. extractionextract the product with ether
  5. washEvapoate the washed
  6. customdried extracts
  7. customto obtain crude crystalline product (16.8 g.), m.p. 102°-5°
  8. customon recrystallization from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-fa681442129346cf9bf718ea622c5a29
Quelldatensatz
uspto-grants-1976_05
Patentnummer
US03959322

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