Pyridine → HCID 15307271, compound

HRID 369047Notes

Reaction equation

HRID 369047 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:17]2[C@@H:16]3[C: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][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: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][CH2:5][C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 6101p-Toluenesulfonic acidHCID 223368Equilin

Product 1

HCID 15307271HCID 15307271, 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), 7-tetraen-17-one in 20 ml of tetrahydrofuran and 2.0 ml of dihydropyran is stirred with 9.6 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. 1.9 g of 3-tetrahydropyranyloxy-estra-1,3,5(10),7-tetraen-17-one is obtained as colorless crystals with a melting point of 147-149° C., [α]D22 =+209.7° (c=0.5% 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-5a4c19b5bf7a41cf9375b6802c149618
Source dataset
uspto-grants-2000_10
Patent number
US06136800

Reaction notes

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