1-Ethynyl-4-propylbenzene → Diphenylacetylene

HRID 1440180Notes

Reaction equation

HRID 1440180 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7](C#C)=[CH:6][CH:5]=1)[CH2:2][CH3:3].[CH2:12](SC1C=CC(I)=CC=1)[CH2:13][CH2:14][CH2:15][CH3:16]>C(NCC)C.[Cu]I>[C:4]1([C:1]#[C:2][C:3]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 27751331-Ethynyl-4-propylbenzeneHCID 189826561-Iodo-4-(pentylthio)benzene

Product 1

HCID 10390Diphenylacetylene

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8021DiethylamineSolvent

Conditions

Temperature
20 °C

Procedure

The product from step 2.4 (2.82 g) and the product from step 2.2 (6.0 g) were mixed in diethylamine (44 ml). Copper (I) iodide (0.026 g) and dichloro di(triphenylphosphine) palladium (0) (0.193 g) were then added and the mixture was then stirred at 20° C. under argon for 16 hrs. Purification by chromatography gave 4.3 g or tolane product, rapt. 43° C.

Workup

  1. customPurification by chromatography

Sources & evidence

ORD record
ord-a6d885e09317419eabc875683bdc806c
Source dataset
uspto-grants-1996_03
Patent number
US05498366

Reaction notes

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