p-Toluenesulfonic acid → HCID 15307268, compound

HRID 850825Notes

Reaction equation

HRID 850825 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[O:20])[CH2:10][CH2:9]4)[CH:6]=[CH:5][C:4]=2[CH:3]=1.[C:21]1(C)C=[CH:25][C:24](S(O)(=O)=O)=[CH:23][CH:22]=1.[O:32]1CCCC1>O1C=CCCC1.C(OCC)(=O)C>[O:32]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[O:1][C:2]1[CH:19]=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[O:20])[CH2:10][CH2:9]4)[CH:6]=[CH:5][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8028TetrahydrofuranHCID 1022253-Hydroxyestra-1,3,5(10),6-tetraen-17-one

Product 1

HCID 15307268HCID 15307268, compound

Reagents, catalysts & solvents 2

HCID 80803,4-dihydro-2H-pyranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 2.6 g of 3-hydroxy-estra-1,3,5(10),6-tetraen-17-one in 26 ml of tetrahydrofuran and 2.6 ml of dihydropyran is stirred with 12.3 mg of para-toluenesulfonic acid for 3 hours at room temperature. Then, it is diluted with ethyl acetate, washed with sodium bicarbonate solution as well as with saturated sodium chloride solution, dried on sodium sulfate and concentrated by evaporation in a vacuum. 3.0 g of 3-tetrahydropyranyloxy-estra-1,3,5(10),6-tetraen-17-one is obtained as colorless crystals.

Workup

  1. washwashed with sodium bicarbonate solution as well as with saturated sodium chloride solution
  2. customdried on sodium sulfate
  3. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-40f88a932e9e4ee3988d32bbecbe111c
Source dataset
uspto-grants-2000_01
Patent number
US06018062

Reaction notes

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