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

HRID 1077161Notes

Reaction equation

HRID 1077161 reaction equation
[BH4-].[Na+].[CH3:3][C@:4]12[CH2:12][CH2:11][C:10]3[C:13]4[CH:14]=[CH:15][C:16]([O:21][CH3:22])=[CH:17][C:18]=4[CH2:19][CH2:20][C:9]=3[C@@H:8]1[CH2:7][CH2:6][C:5]2=[O:23].C(O)(=O)C>C(O)C>[CH3:3][C@:4]12[CH2:12][CH2:11][C:10]3[C:13]4[CH:14]=[CH:15][C:16]([O:21][CH3:22])=[CH:17][C:18]=4[CH2:19][CH2:20][C:9]=3[C@@H:8]1[CH2:7][CH2:6][C@@H:5]2[OH:23]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 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 44.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Add sodium borohydride (0.5 g.) in ethanol (60 cc.) with stirring to 13-methyl-3-methoxygona-1,3,5(10),8-tetraen-17-one (2.0 g.) in ethanol (150 cc.) at 14°-15°. Leave the mixture at room temperature for 1 hour, acidify with glacial acetic acid and evaporate to dryness under reduced pressure. Treat the residue with water, ether-extract and wash and dry. Evaporate the extracts. Recrystallize the residue from a mixture of methanol (15 cc.) and water (3 cc.) to obtain the title product (0.90 g.), m.p. 110°-2°. A sample sublimes at 110°/10-4 mm. and has an ultra-violet absorption peak at 277 mμ (ε 14,500).

Workup

  1. customLeave the mixture at room temperature for 1 hour
  2. customevaporate to dryness under reduced pressure
  3. additionTreat the residue with water, ether-
  4. extractionextract
  5. washwash
  6. customdry
  7. customEvaporate the extracts
  8. customRecrystallize the residue
  9. additionfrom a mixture of methanol (15 cc.) and water (3 cc.)

Sources & evidence

ORD record
ord-7d9f639c32aa4826b975190d746b9bf8
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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