Pyridine → 3-Tetrahydropyranyloxy-8alpha-estra-1,3,5(10)-trien-17-one

HRID 850845Notes

Reaction equation

HRID 850845 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)[CH2:6][CH2:5][C:4]=2[CH:3]=1.C1(C)C=CC(S(O)(=O)=[O:28])=CC=1.N1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>O1CCCC1.O1C=CCCC1.C(OCC)(=O)C>[O:28]1[CH2:37][CH2:36][CH2:35][CH2:34][CH:33]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)[CH2:6][CH2:5][C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 6101p-Toluenesulfonic acidHCID 9547221(8α)-3-Hydroxyestra-1,3,5(10)-trien-17-one

Product 1

HCID 156181363-Tetrahydropyranyloxy-8alpha-estra-1,3,5(10)-trien-17-one

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 80803,4-dihydro-2H-pyranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 2.0 g of 3-hydroxy-8α-estra-1,3,5(10)-trien -17-one in 20 ml of tetrahydrofuran and 2.0 ml of dihydropyran is stirred with 15 mg of para-toluenesulfonic acid for 24 hours at room temperature. Then, 0.3 ml of pyridine is added, diluted with ethyl acetate, washed with sodium bicarbonate solution as well as with saturated sodium chloride solution, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with hexane/acetone. 2.2 g of 3-tetrahydropyranyloxy-8α-estra-1,3,5(10)-trien-17-one is obtained as colorless crystals with a melting point of 153-155° C., [α]D22 =+47.5° (c=0.53% in pyridine).

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
  4. customchromatographed on silica gel with hexane/acetone

Sources & evidence

ORD record
ord-a74c0120670d449eb9b4da70d07c7187
Source dataset
uspto-grants-2000_01
Patent number
US06018062

Reaction notes

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