Phenylacetylene → 1-[5-Methoxy-2-(phenylethynyl)phenyl]-2-propanone

HRID 543437Notes

Reaction equation

HRID 543437 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][C:11](=[O:13])[CH3:12].[C:14]1([C:20]#[CH:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(N(CC)CC)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:21]#[C:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:3]([CH2:10][C:11](=[O:13])[CH3:12])[CH:4]=1

Participants

5

Reactant 2

HCID 10821PhenylacetyleneHCID 139107882-Iodo-5-methoxyphenyl-2-propanone

Product 1

HCID 140254751-[5-Methoxy-2-(phenylethynyl)phenyl]-2-propanoneYield 112.1%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Procedure

A solution of 5.5 g (18.9 mmole) 2-iodo-5-methoxyphenyl-2-propanone (18.9 mmole), 4.15 ml (37.8 mmole) of phenylacetylene, 0.037 g cuprous iodide (1 mole percent) and 0.066 g of bis(triphenylphosphine)palladium (II) chloride (5 mole percent) in 60 ml of triethylamine was stirred for 18 hours under N2 at room temperature. The mixture was partitioned between water and ether. The ether layer was washed successively with cold hydrochloric acid solution, washed and brine. It was dried over MgSO4 and the solvent evaporated in vacuo to give 5.6 g (100% yield) of brown crystals. Recrystallization from methylcyclohexane afforded pure 1-[5-(methoxy)-2-(phenylethynyl)phenyl]-2-propanone, mp 60°-62° C.

Workup

  1. customThe mixture was partitioned between water and ether
  2. washThe ether layer was washed successively with cold hydrochloric acid solution
  3. washwashed
  4. dry with materialIt was dried over MgSO4
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-5eb66a4112c54942ae530b30b4761780
Source dataset
uspto-grants-1987_04
Patent number
US04661635

Reaction notes

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