Pyridine → 13-Ethyl-17beta-(2-hydroxyethoxy)-3-methoxygona-1,3,5(10)-triene methane sulfonate

HRID 1415068Notes

Reaction equation

HRID 1415068 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH:13]=[CH:14][C:15]([O:20][CH3:21])=[CH:16][C:17]=4[CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[O:22][CH2:23][CH2:24][OH:25])[CH3:2].N1C=CC=CC=1.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>CO.O>[CH3:32][S:33]([OH:35])(=[O:20])=[O:34].[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH:13]=[CH:14][C:15]([O:20][CH3:21])=[CH:16][C:17]=4[CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[O:22][CH2:23][CH2:24][OH:25])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 6814377113-Ethyl-17beta-(2-hydroxyethoxy)-3-methoxygona-1,3,5(10)-triene

Product 1

HCID 8673349313-Ethyl-17beta-(2-hydroxyethoxy)-3-methoxygona-1,3,5(10)-triene methane sulfonate

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 962WaterSolvent

Procedure

Stir a cooled solution of 344 mg. of dl-13-ethyl-17β-(2-hydroxyethoxy)-3-methoxygona-1,3,5(10)-triene in 2 ml. of pyridine (acetone-dry ice bath) and add dropwise 0.14 ml. of methanesulfonyl chloride. After 2 hours bring reaction mixture to room temperature. Mix with ice and water and a few drops of methanol to obtain a crystalline precipitate. Recrystallize this to obtain dl-13-ethyl-17β-(2-hydroxyethoxy)-3-methoxygona-1,3,5(10)-triene methane sulfonate from methanol (310 mg); m.p. 104°.

Workup

  1. customreaction mixture to room temperature
  2. customto obtain a crystalline precipitate
  3. customRecrystallize

Sources & evidence

ORD record
ord-4e91a78cdd944192a06409775b9caf53
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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