HCID 70388515, compound → Gestodene

HRID 2413546Notes

Reaction equation

HRID 2413546 reaction equation
C[O:2][C:3]1[CH2:21][CH2:20][C@H:19]2[C:5](=[CH:6][CH2:7][C@@H:8]3[C@@H:18]2[CH2:17][CH2:16][C@@:13]2([CH2:14][CH3:15])[C@H:9]3[C@@H:10](OC(=O)C(C)(C)C)[CH2:11][C:12]2=[O:22])[CH:4]=1.[C-:30]#[C-:31].[Li+].[Li+]>>[C:30]([C@:12]1([OH:22])[CH:11]=[CH:10][C@H:9]2[C@H:8]3[C@H:18]([CH2:17][CH2:16][C@:13]12[CH2:14][CH3:15])[C@@H:19]1[C:5](=[CH:4][C:3](=[O:2])[CH2:21][CH2:20]1)[CH2:6][CH2:7]3)#[CH:31]

Participants

3

Reactant 2

HCID 70388515HCID 70388515, compoundHCID 178462446HCID 178462446, compound

Product 1

HCID 3033968Gestodene

Procedure

Analogously to Example 1(b), 2.8 g of 3-methoxy-18-methyl-15α-trimethylacetoxy-3,5-estradien-17-one is reacted with lithium acetylide and worked up. Recrystallization from acetone/hexane yields 1.6 g of 17α-ethynyl-17β-hydroxy-18-methyl-4,15-estradien-3-one, melting point 197° C.

Workup

  1. customRecrystallization from acetone/hexane

Sources & evidence

ORD record
ord-2daa17118fcf4a41877c183949c35dcb
Source dataset
uspto-grants-1988_01
Patent number
US04719054

Reaction notes

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