Hydrochloric Acid → 1-Hydroxy-3-methoxyestra-1,3,5(10)-trien-17-one

HRID 839759Notes

Reaction equation

HRID 839759 reaction equation
C([O:4][C:5]1[C:22]2[C@@H:21]3[C@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C:16](=[O:23])[CH2:15][CH2:14]4)[CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([O:24][CH3:25])[CH:6]=1)(=O)C.O.Cl>[OH-].[K+]>[OH:4][C:5]1[C:22]2[C@@H:21]3[C@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C:16](=[O:23])[CH2:15][CH2:14]4)[CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([O:24][CH3:25])[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 544622991-Acetoxy-3-methoxyestra-1,3,5(10)-trien-17-one

Product 1

HCID 545489061-Hydroxy-3-methoxyestra-1,3,5(10)-trien-17-one

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

A solution of 1-acetoxy-3-methoxyestra-1,3,5(10)-trien-17-one (7.0 g, 20.5 mM) in 150 ml of 5% anhydrous methanolic potassium hydroxide is stirred at room temperature for 1 hr. The resulting dark purple solution is added to 700 ml of cold H2O and acidified with 10% HCl to give a white solid which is filtered and recrystallized from acetone-H2O to give 1-hydroxy-3-methoxyestra-1,3,5(10)-trien-17-one, yield 5.4 g (88%), m.p. 220°-222°. Further recrystallization from ethyl acetate gives a product with a m.p. 226°-229°.

Workup

  1. customto give a white solid which
  2. filtrationis filtered
  3. customrecrystallized from acetone-H2O

Sources & evidence

ORD record
ord-800ea408627a4278b12efffdcf18ed77
Source dataset
uspto-grants-1978_06
Patent number
US04096253

Reaction notes

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