HCID 67362260, compound → Gestodene

HRID 2413535Notes

Reaction equation

HRID 2413535 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]#[C-:23].[Li+].[Li+]>>[CH3:1][CH2:2][C@@:3]12[C@:4]([OH:21])([C:22]#[CH:23])[CH:5]=[CH:6][C@H:7]1[C@@H:8]1[CH2:9][CH2:10][C:11]3[C@@H:16]([C@H:17]1[CH2:18][CH2:19]2)[CH2:15][CH2:14][C:13](=[O:20])[CH:12]=3

Participants

3

Reactant 2

HCID 67362260HCID 67362260, compoundHCID 178462446HCID 178462446, compound

Product 1

HCID 3033968GestodeneYield 75%

Procedure

By treating 18-methyl-4,15-estradiene-3,17-dione (Formula III: Y=O, A-B=CH=CH) with lithium acetylide, gestodene is obtained in a high yield of about 75%. However, this method is usable only for amounts of starting material compounds up to 100 g; ethynylation in this manner therefore cannot be performed on an industrial scale. Moreover, it has been found that the 18-methyl-4,15-estradiene-3,17-dione starting material can have a sensitizing effect in case of skin contact, consequently protective measures must be observed when handling 18-methyl-4,15-estradiene-3,17-dione.

Sources & evidence

ORD record
ord-a1f76ea2329045bd866eba88a67895f1
Source dataset
uspto-grants-1988_01
Patent number
US04719054

Reaction notes

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