Pyridine → HCID 15307277, compound

HRID 369053Notes

Reaction equation

HRID 369053 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:17]2[C:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH: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:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH: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 108908813-HYDROXY-ESTRA-1,3,5(10),9(11)-TETRAEN-17-ONE

Product 1

HCID 15307277HCID 15307277, compound

Reagents, catalysts & solvents 3

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

Procedure

A suspension of 2.0 g of 3-hydroxy-estra-1,3,5(10),9(11)-tetraen-17-one in 20 ml of tetrahydrofuran and 3.0 ml of dihydropyran is stirred with 15 mg of para-toluenesulfonic acid for 29 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/triethylamine. 2.3 g of 3-tetrahydropyranyloxy-estra-1,3,5(10),9(11)-tetraen-17-one is obtained as a colorless oil, [α]D22 =+122.5° (c=0.515% 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/triethylamine

Sources & evidence

ORD record
ord-d988435dc93841ebbb736b16bbcdfde0
Source dataset
uspto-grants-2000_10
Patent number
US06136800

Reaction notes

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