Tetrahydrofuran → Phthalimide

HRID 1527611Notes

Reaction equation

HRID 1527611 reaction equation
C([N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15])CC#C.O1CCCC1.[I-].C1C=CC=CC=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I.C(N(CC)CC)C>[C:9]1(=[O:10])[NH:5][C:6](=[O:15])[C:7]2=[CH:14][CH:13]=[CH:12][CH:11]=[C:8]12

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 11171619N-(3-Butynyl)phthalimideHCID 22498004HCID 22498004, compound

Product 1

HCID 6809PhthalimideYield 167%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

To 535 mg of dichlorobis(triphenylphosphine)palladium, 145 mg of copper iodide, and 3.00 g of N-(3-butynyl)phthalimide were added 35 ml of tetrahydrofuran, 3.06 g of benzene iodide, and 9.0 ml of triethylamine in a nitrogen atmosphere, and the mixture was stirred under reflux for 4 hours. After the stirring, the reaction mixture was cooled to room temperature and the solids were filtered. After concentrating the filtrate, the residue was purified by column chromatography (Wakogel C-200; toluene:ethyl acetate=4:1) to give 3.70 g of a phthalimide compound.

Workup

  1. temperatureunder reflux for 4 hours
  2. filtrationthe solids were filtered
  3. concentrationAfter concentrating the filtrate
  4. customthe residue was purified by column chromatography (Wakogel C-200; toluene:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-de507bbfdea140ce9e9dc224e9a4a284
Source dataset
uspto-grants-2015_07
Patent number
US09089139B2

Reaction notes

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