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

HRID 1415032Notes

Reaction equation

HRID 1415032 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:22]=[CH:21][C:20]2[C:19]3[CH2:18][CH2:17][C@@:15]4([CH3:16])[C@@H:11]([CH2:12][CH2:13][C:14]4=[O:23])[C:10]=3[CH2:9][CH2:8][C:7]=2[CH:6]=1.C(O)(=O)C.O>C(O)C>[CH3:3][O:4][C:5]1[CH:22]=[CH:21][C:20]2[C:19]3[CH2:18][CH2:17][C@@:15]4([CH3:16])[C@@H:11]([CH2:12][CH2:13][C@@H:14]4[OH:23])[C:10]=3[CH2:9][CH2:8][C:7]=2[CH:6]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 11055125Estra-1,3,5(10),8-tetraen-17-one, 3-methoxy-

Product 1

HCID 110552063-Methoxyestra-1,3,5(10),8-tetraen-17beta-olYield 93.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add sodium borohydride (8.5 g) to 3-methoxyestra-1,3,5(10),8-tetraen-17-one (40 g) in ethanol (500 ml) and reflux the mixture for 90 minutes. Acidify the cooled solution with acetic acid, add water and extract with benzene. Wash, dry and evaporate the organic extract to obtain dl-3-methoxyestra-1,3,5(10),8-tetraen-17β-ol (37.5 g), m.p. 130°-133°; ultraviolet absorption peak at 280 mμ(ε16,100); infrared maxima at 3.1 μ, 3.58 μ, 6.25 μ, 6.4 μ, 6.7 μ.

Workup

  1. temperaturereflux the mixture for 90 minutes
  2. extractionextract with benzene
  3. washWash
  4. customdry
  5. customevaporate the
  6. extractionorganic extract

Sources & evidence

ORD record
ord-b6bde9edb02d46ae8b75ae44916aed84
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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