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

HRID 1077212Notes

Reaction equation

HRID 1077212 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-24781c50940a43d1867811307a4fc7e7
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

Loading…