1-Ethynyl-4-methoxybenzene → 4-Methoxy-4'-(1-propynyl)tolan

HRID 465891Notes

Reaction equation

HRID 465891 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[CH:10])=[CH:5][CH:4]=1.[C:11]([C:14]1[CH:19]=[CH:18][C:17](I)=[CH:16][CH:15]=1)#[C:12][CH3:13]>C(NCC)C.[Cu](I)I>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:17]2[CH:18]=[CH:19][C:14]([C:11]#[C:12][CH3:13])=[CH:15][CH:16]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 2510201-Ethynyl-4-methoxybenzeneHCID 121767134-(1-Propynyl)iodobenzene

Product 1

HCID 598753514-Methoxy-4'-(1-propynyl)tolan

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8021DiethylamineSolvent

Procedure

4-Methoxyphenyl acetylene (2.65 g, 0.02 mol) and 4-(1-propynyl)iodobenzene (5.0 g, 0.02 mol) were dissolved in diethylamine (20 ml), and then added copper iodide (0.06 g) and dichlorobistriphenylphosphinepalladium dichloride (0.21 g) were added. The resulting mixture was subjected to reaction and purification operations in the same manners as in Example 1, to obtain the objective 4-methoxy-4'-(1-propynyl)tolan (No. 297) (1.35 g).

Workup

  1. customThe resulting mixture was subjected to reaction and purification operations in the same manners as in Example 1

Sources & evidence

ORD record
ord-24a7db5658fb4840aea215ec309a8e30
Source dataset
uspto-grants-1992_10
Patent number
US05154851

Reaction notes

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