4-(1-Propynyl)iodobenzene → HCID 178439006, compound

HRID 465888Notes

Reaction equation

HRID 465888 reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[C:18]([C:21]1[CH:26]=[CH:25][C:24](I)=[CH:23][CH:22]=1)#[C:19][CH3:20]>C(NCC)C.[Cu](I)I>[CH2:18]([C@H:21]1[CH2:26][CH2:25][C@H:24]([C:15]2[CH:16]=[CH:17][C:12]([C:11]#[C:10][C:7]3[CH:6]=[CH:5][C:4]([CH2:1][CH2:2][CH3:3])=[CH:9][CH:8]=3)=[CH:13][CH:14]=2)[CH2:23][CH2:22]1)[CH2:19][CH3:20]

Participants

5

Reactant 2

HCID 121767134-(1-Propynyl)iodobenzeneHCID 178447947HCID 178447947, compound

Product 1

HCID 178439006HCID 178439006, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8021DiethylamineSolvent

Procedure

Trans-4-propylcyclohexylphenylacetylene (2.3 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-(trans-4-propylcyclohexyl)-4'-(1-propyl)tolan (compound No. 57) (1.8 g). (CS point: 118.9° C., SN point: 127.4° C., NI point: 245.1° C.)

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-4281b35f24ea457c922015a20935633b
Source dataset
uspto-grants-1992_10
Patent number
US05154851

Reaction notes

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