Pyridine → HCID 15307274, compound

HRID 369050Notes

Reaction equation

HRID 369050 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:17]2[C:16]3[CH2:15][CH2:14][C@@:12]4([CH3:13])[C@@H:8]([CH2:9][CH2:10][C:11]4=[O:20])[C:7]=3[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[CH2:15][CH2:14][C@@:12]4([CH3:13])[C@@H:8]([CH2:9][CH2:10][C:11]4=[O:20])[C:7]=3[CH2:6][CH2:5][C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 6101p-Toluenesulfonic acidHCID 64514728,9-Dehydroestrone

Product 1

HCID 15307274HCID 15307274, 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),8-tetraen-17-one in 20 ml of tetrahydrofuran and 2.0 ml of dihydropyran is stirred with 9.4 mg of para-toluenesulfonic acid for 3 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. 2.4 g of 3-tetrahydropyranyloxy-estra-1,3,5(10),8-tetraen-17-one is obtained as colorless crystals with a melting point of 122-125° C., [α]D22 =+0.00° (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-ba6a0d64a1d944519e6b388b13fddc0e
Source dataset
uspto-grants-2000_10
Patent number
US06136800

Reaction notes

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