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

HRID 1414979Notes

Reaction equation

HRID 1414979 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. Evaporate 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. customEvaporate the
  6. washwashed
  7. customdried extracts
  8. customto obtain crude crystalline product (16.8 g.), m.p. 102°-5°
  9. customon recrystallization from acetonitrile

Sources & evidence

ORD record
ord-02e0c299802a438583029fb7b48f3f30
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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