Pyridine → HCID 67362893, compound

HRID 2413537Notes

Reaction equation

HRID 2413537 reaction equation
[CH3:1][CH2:2][C@:3]12[CH2:19][CH2:18][C@H:17]3[C@@H:8]([CH2:9][CH2:10][C:11]4[C@@H:16]3[CH2:15][CH2:14][C:13](=[O:20])[CH:12]=4)[C@@H:7]1[CH:6]=[CH:5][C:4]2=[O:21].[C:22]1(C)C=CC(S(O)(=O)=O)=CC=1.N1C=CC=CC=1>O1CCOCC1.C(OC)(OC)OC>[CH3:22][O:20][C:13]1[CH2:14][CH2:15][C@H:16]2[C:11](=[CH:10][CH2:9][C@@H:8]3[C@@H:17]2[CH2:18][CH2:19][C@@:3]2([CH2:2][CH3:1])[C@H:7]3[CH:6]=[CH:5][C:4]2=[O:21])[CH:12]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 6101p-Toluenesulfonic acidHCID 67362260HCID 67362260, compound

Product 1

HCID 67362893HCID 67362893, compoundYield 1,009.8%

Reagents, catalysts & solvents 2

HCID 9005Trimethyl orthoformateSolventHCID 312751,4-DioxaneSolvent

Procedure

Under argon, 20.0 g of 18-methyl-4,15-estradiene-3,17-dione in 100 ml of 1,4-dioxane and 100 ml of trimethyl orthoformate is agitated with 800 mg of p-toluenesulfonic acid at 50° C. After 2.5 hours, 10 ml of pyridine is added and the solution extensively distilled under vacuum. The residue is dissolved in ethyl acetate, washed with water, and dried. Chromatography of the crude product with 0-20% ethyl acetate-hexane yields 14.0 g of 3-methoxy-18-methyl-3,5,15-estratrien-17-one, melting point 162.1° C. (from methanol).

Workup

  1. distillationthe solution extensively distilled under vacuum
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-24ed87cd89e94a3d8902cb2769564503
Source dataset
uspto-grants-1988_01
Patent number
US04719054

Reaction notes

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