5-Bromo-2-ethoxypyridine → 1-(4-Propylphenyl)-2-(2-ethoxy-pyridine-5-yl)-acetylene

HRID 1590800Notes

Reaction equation

HRID 1590800 reaction equation
C([Mg]Br)C.[CH2:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]#[CH:15])=[CH:10][CH:9]=1)[CH2:6][CH3:7].[CH2:16]([O:18][C:19]1[CH:24]=[CH:23][C:22](Br)=[CH:21][N:20]=1)[CH3:17]>CCOCC>[CH2:5]([C:8]1[CH:9]=[CH:10][C:11]([C:14]#[C:15][C:22]2[CH:23]=[CH:24][C:19]([O:18][CH2:16][CH3:17])=[N:20][CH:21]=2)=[CH:12][CH:13]=1)[CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 8172375-Bromo-2-ethoxypyridineHCID 27751331-Ethynyl-4-propylbenzeneHCID 178418443HCID 178418443, compound

Product 1

HCID 197684371-(4-Propylphenyl)-2-(2-ethoxy-pyridine-5-yl)-acetylene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

0.05 m of ethylmagnesium bromide in ether are added to a mixture of 0.05 m of 4-propylphenylacetylene at 0°-10°. The mixture is stirred for 4 hours at room temperature and then a solution of 0.05 m of 2-ethoxy-5-bromopyridine and 0.5 g of NiCl2 (Ph3P)2 in ether is added. After stirring for 6 hours at room temperature and customary work-up 1-(4-propylphenyl)-2-(2-ethoxy-pyridine-5-yl)-acetylene is obtained.

Workup

  1. stirringAfter stirring for 6 hours at room temperature

Sources & evidence

ORD record
ord-3c2eb9e2e92e4d70be1e1e9e1f068d2d
Source dataset
uspto-grants-1993_04
Patent number
US05204477

Reaction notes

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