p-Toluenesulfonic acid → Estra-1,3,5(10),15-tetraen-17-one

HRID 650333Notes

Reaction equation

HRID 650333 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](O)=[CH:13][C:12]=2[CH2:11][C@H:10]4CCCCCO)[O:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.O>[CH3:5][C@:4]12[CH2:20][CH2:19][C@H:18]3[C@@H:9]([CH2:10][CH2:11][C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=43)[C@@H:6]1[CH:7]=[CH:8][C:3]2=[O:2]

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 22796830Estra-1,3,5(10),15-tetraen-17-one

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 ⅓ 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
  2. washwashed neutral
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-f76fd119aadf43318a0f15258d1a34e2
Source dataset
uspto-grants-2001_08
Patent number
US06271403B1

Reaction notes

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