Pyridine → HCID 67362053, compound

HRID 2413540Notes

Reaction equation

HRID 2413540 reaction equation
[C:1]([O:4][C@@H:5]1[C@H:11]2[C@H:12]3[C@H:21]([CH2:22][CH2:23][C@:8]2([CH2:9][CH3:10])[C:7](=[O:25])[CH2:6]1)[C@@H:20]1[C:15](=[CH:16][C:17](=[O:24])[CH2:18][CH2:19]1)[CH2:14][CH2:13]3)(=[O:3])[CH3:2].C(OCC)(OCC)O[CH2:28][CH3:29].C1(C)C=CC(S(O)(=O)=O)=CC=1.N1C=CC=CC=1>O1CCOCC1.CCOCC>[C:1]([O:4][C@@H:5]1[C@H:11]2[C@H:12]3[C@H:21]([CH2:22][CH2:23][C@:8]2([CH2:9][CH3:10])[C:7](=[O:25])[CH2:6]1)[C@@H:20]1[C:15]([CH:16]=[C:17]([O:24][CH2:28][CH3:29])[CH2:18][CH2:19]1)=[CH:14][CH2:13]3)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformateHCID 67361589HCID 67361589, compound

Product 1

HCID 67362053HCID 67362053, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

Under argon, 2.0 g of 15α-acetoxy-18-methyl-4-estrene-3,17-dione in 60 ml of dioxane is agitated at room temperature for 20 hours with 6 ml of triethyl orthoformate and 40 mg of p-toluenesulfonic acid. After adding 2 ml of pyridine, the mixture is diluted with ether, washed with water, and dried. The crude product is recrystallized from acetone/hexane. Yield: 1.6 g of 15α-acetoxy-3-ethoxy-18-methyl-3,5-estradien-17-one. Melting point: 202° C.

Workup

  1. washwashed with water
  2. customdried
  3. customThe crude product is recrystallized from acetone/hexane

Sources & evidence

ORD record
ord-b3aa82fe677d4f7ba0235dd4265c371f
Source dataset
uspto-grants-1988_01
Patent number
US04719054

Reaction notes

Loading…