Diethylamine → 4-(4-Propylphenyl)-4'-(1-propynyl)tolan

HRID 465890Notes

Reaction equation

HRID 465890 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[CH:2].[C:18]([C:21]1[CH:26]=[CH:25][C:24](I)=[CH:23][CH:22]=1)#[C:19]C.[CH2:28](NCC)C>[Cu](I)I>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]#[C:16][C:17]3[CH:23]=[CH:22][C:21]([C:26]#[C:25][CH3:24])=[CH:18][CH:19]=3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)[CH2:2][CH3:28]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 121767134-(1-Propynyl)iodobenzeneHCID 198149114-Ethynyl-4'-propyl-1,1'-biphenyl

Product 1

HCID 867461894-(4-Propylphenyl)-4'-(1-propynyl)tolan

Reagents, catalysts & solvents 1

HCID 83717Copper iodideCatalyst

Procedure

4-Ethynyl-4'-propylbiphenyl (prepared according to the method disclosed in Japanese patent application laid-open No. Sho 58-110527/1983) (2.2 g, 0.01 mol) and 4-(1-propynyl)iodobenzene (2.4 g, 0.01 mol) were dissolved in diethylamine (20 ml), and then copper iodide (0.11 g, 0.15 mmol) and dichlorobistriphenylphosphinepalladium dichloride (0.21 g, 0.3 mmol) were added. The resulting mixture was subjected to reaction and purification operation in the same manner as in Example 1, to obtain the objective 4-(4-propylphenyl)-4'-(1-propynyl)tolan (compound

Workup

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

Sources & evidence

ORD record
ord-3bde6962d55944a9a8362f04d41b31f7
Source dataset
uspto-grants-1992_10
Patent number
US05154851

Reaction notes

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