Acetylene → HCID 86733488, compound

HRID 1415038Notes

Reaction equation

HRID 1415038 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

Stir dl-13-ethyl-3-methoxy-6-methylgona-2,5(10) -dien-17-one (3.6 g) in dimethylacetamide (35 cc) in a stream of acetylene for one-half hour. Add lithium acetylide-ethylenediamine (2.7 g) and stir for 4 hours. Pour into ice water, extract with ether and isolate the dl-13-ethyl-3-methoxy-17α-ethynyl-17β-hydroxy-6-methylgona-2,5(10)-diene as a gum (3.5 g), λmax. NaCl 2.90 μ, 3.05 μ, 5.90 μ, 6.03 μ.

Workup

  1. extractionextract with ether

Sources & evidence

ORD record
ord-32bc5c889af04564988fb30d6cf45569
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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