HCID 68143291, compound → 13-Ethyl-3-methoxy-17alpha-ethynyl-17-hydroxy-6-methylgona-2,5(10)-diene

HRID 1415051Notes

Reaction equation

HRID 1415051 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH2:13][CH:14]=[C:15]([O:21][CH3:22])[CH2:16][C:17]=4[CH:18]([CH3:20])[CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C:4]2=[O:23])[CH3:2].[C-]#[C-].[Li+].[Li+].[CH2:28](N)[CH2:29]N>CC(N(C)C)=O>[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH2:13][CH:14]=[C:15]([O:21][CH3:22])[CH2:16][C:17]=4[CH:18]([CH3:20])[CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@:4]2([C:28]#[CH:29])[OH:23])[CH3:2]

Participants

4

Reactant 2

HCID 68143291HCID 68143291, compoundHCID 178511344HCID 178511344, compound

Product 1

HCID 8673348813-Ethyl-3-methoxy-17alpha-ethynyl-17-hydroxy-6-methylgona-2,5(10)-dieneYield 89.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Dissolve dl-13-ethyl-6-methyl-3-methoxygona-2,5(10)-dien-17-one (3.6 g) in dimethylacetamide (35 ml) and stir in a stream of acteylene for 0.5 hour. Add solid lithium acetylide-ethylenediamine (2.7 g) and stir the solution for 4 hours. Pour the reaction mixture onto ice, extract with ether, wash the ether layer with water, dry, and evaporate to obtain dl-13-ethyl-3-methoxy-6-methyl-17α-ethynyl-17-hydroxygona-2,5(10)-diene (3.5 g) as a gum; infrared absorption peaks (sodium chloride) at 2.90 μ, 3.05 μ, 5.90 μ, 6.03 μ.

Workup

  1. stirringstir the solution for 4 hours
  2. additionPour the reaction mixture onto ice
  3. extractionextract with ether
  4. washwash the ether layer with water
  5. customdry
  6. customevaporate

Sources & evidence

ORD record
ord-4985fac4efab40f298fd9f2267702b80
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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