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

HRID 1077162Notes

Reaction equation

HRID 1077162 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fa681442129346cf9bf718ea622c5a29
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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