p-Toluenesulfonic acid → 3-Hydroxy-7alpha-(5-hydroxypentyl)-estra-1,3,5(10),15-tetraen-17-one

HRID 1603328Notes

Reaction equation

HRID 1603328 reaction equation
C1CO[C:3]2([CH:8]=[CH:7][C@H:6]3[C@H:9]4[C@H:18]([CH2:19][CH2:20][C@:4]23[CH3:5])[C:17]2[CH:16]=[CH:15][C:14]([OH:21])=[CH:13][C:12]=2[CH2:11][C@H:10]4[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][OH:27])[O:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.O>[OH:21][C:14]1[CH:15]=[CH:16][C:17]2[C@@H:18]3[C@H:9]([C@H:6]4[C@@:4]([CH2:20][CH2:19]3)([CH3:5])[C:3](=[O:2])[CH:8]=[CH:7]4)[C@H:10]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][OH:27])[CH2:11][C:12]=2[CH:13]=1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 5702379917,17-Ethylenedioxy-7alpha-(5-hydroxypentyl)-estra-1,3,5(10),15-tetraen-3-ol

Product 1

HCID 158381633-Hydroxy-7alpha-(5-hydroxypentyl)-estra-1,3,5(10),15-tetraen-17-oneYield 98.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 36.12 g of 17,17-ethylenedioxy-7α-(5-hydroxypentyl)-estra-1,3,5(10),15-tetraen-3-ol in 958 ml of acetone and 111 ml of water is stirred for 2 hours at room temperature with 2.76 g of para-toluenesulfonic acid. Then, it is concentrated by evaporation in a vacuum to 1/3 of the volume, taken up with ethyl acetate, washed neutral, dried on sodium sulfate and concentrated by evaporation in a vacuum. 31.7 g of 3-hydroxy-7α-(5-hydroxypentyl)-estra-1,3,5(10),15-tetraen-17-one is obtained as crystals with a melting point of 194-196° C.

Workup

  1. concentrationThen, it is concentrated by evaporation in a vacuum to 1/3 of the volume
  2. washwashed neutral
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-2a65bb9f5b5f474e9ea0c93566f7b281
Source dataset
uspto-grants-1999_11
Patent number
US05986115

Reaction notes

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