p-Toluenesulfonic acid → 3-Benzyloxy-7alpha-(5-hydroxypentyl)-estra-1,3,5(10),15-tetra-en-17-one

HRID 650341Notes

Reaction equation

HRID 650341 reaction equation
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:18]3(OCC[O:27]3)[CH:17]=[CH:16]4)[C@H:13]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][OH:36])[CH2:12][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.O.C(OCC)C>[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:18](=[O:27])[CH:17]=[CH:16]4)[C@H:13]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][OH:36])[CH2:12][C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 571990303-Benzyloxy-17,17-ethylenedioxy-7alpha-(5-hydroxypentyl)-estra-1,3,5(10),15-tetraene

Product 1

HCID 572721663-Benzyloxy-7alpha-(5-hydroxypentyl)-estra-1,3,5(10),15-tetra-en-17-oneYield 85.1%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 32.8 g of 3-benzyloxy-17,17-ethylenedioxy-7α-(5-hydroxypentyl)-estra-1,3,5(10),15-tetraene in 328 ml of acetone and 32.8 ml of water is stirred at room temperature with 1.033 g of para-toluenesulfonic acid for 2 hours. Then, it is diluted with diethyl ether, washed with sodium bicarbonate and water, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with dichloromethane acetone. 25.4 g of 3-benzyloxy-7α-(5-hydroxypentyl)-estra-1,3,5(10),15-tetraen-17-one is obtained.

Workup

  1. washwashed with sodium bicarbonate and water
  2. customdried on sodium sulfate
  3. concentrationconcentrated by evaporation in a vacuum
  4. customchromatographed on silica gel with dichloromethane acetone

Sources & evidence

ORD record
ord-281db49a081f45c4b84e4bdd909980c2
Source dataset
uspto-grants-2001_08
Patent number
US06271403B1

Reaction notes

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