Potassium Hydroxide → 17,17-Ethylenedioxy-7alpha-(5-hydroxypentyl)-estra-1,3,5(10),15-tetraen-3-ol

HRID 361643Notes

Reaction equation

HRID 361643 reaction equation
C([O:4][C:5]1[CH:22]=[CH:21][C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C:14]3([O:26][CH2:25][CH2:24][O:23]3)[C@H:13](Br)[CH2:12]4)[C@H:9]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33]C(=O)C)[CH2:8][C:7]=2[CH:6]=1)(=O)C.[OH-].[K+]>CS(C)=O.CO>[CH2:25]1[CH2:24][O:23][C:14]2([CH:13]=[CH:12][C@H:11]3[C@H:10]4[C@H:19]([CH2:18][CH2:17][C@:15]23[CH3:16])[C:20]2[CH:21]=[CH:22][C:5]([OH:4])=[CH:6][C:7]=2[CH2:8][C@H:9]4[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][OH:33])[O:26]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 158381613-Acetoxy-7alpha-(5-acetoxypentyl)-16alpha-bromo-17,17-ethylenedioxy-estra-1,3,5(10)-triene

Product 1

HCID 5702379917,17-Ethylenedioxy-7alpha-(5-hydroxypentyl)-estra-1,3,5(10),15-tetraen-3-olYield 68.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

A solution of 74.1 g of 3-acetoxy-7α-(5-acetoxypentyl)-16α-bromo-17,17-ethylenedioxy-estra-1,3,5(10)-triene in 740 ml of dimethyl sulfoxide and 74 ml of methanol is stirred with 74 g of potassium hydroxide for 7.5 hours at a bath temperature of 85° C. Then, it is precipitated with ice/water/common salt, taken up with ethyl acetate, washed neutral, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with hexane/ethyl acetate. 36.12 g of pure 17,17-ethylenedioxy-7α-(5-hydroxypentyl)-estra-1,3,5(10),15-tetraen-3-ol is obtained as foam.

Workup

  1. customThen, it is precipitated with ice/water/common salt
  2. washwashed neutral
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation in a vacuum
  5. customchromatographed on silica gel with hexane/ethyl acetate

Sources & evidence

ORD record
ord-9d6f724e5d684241bda96b4adb070203
Source dataset
uspto-grants-1999_02
Patent number
US05866560

Reaction notes

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