Acetylene → HCID 86733488, compound

HRID 1077231Notes

Reaction equation

HRID 1077231 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.[C-]#[C-].[Li+].[Li+].[CH2:30](N)[CH2:31]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:30]#[CH:31])[OH:23])[CH3:2]

Participants

5

Reactant 3

HCID 6326AcetyleneHCID 68143291HCID 68143291, compoundHCID 178511344HCID 178511344, compound

Product 1

HCID 86733488HCID 86733488, compoundYield 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 acetylene 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. additionPour the reaction mixture onto ice
  2. extractionextract with ether
  3. washwash the ether layer with water
  4. customdry
  5. customevaporate

Sources & evidence

ORD record
ord-8cc3a7d9eb68443f859265f665982703
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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