Tetrahydrofuran → HCID 12134165, compound

HRID 2041866Notes

Reaction equation

HRID 2041866 reaction equation
O1CCCC1.I[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:13]([N:17]1[C:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:27])[CH2:14][C:15]#[CH:16]>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:7]1([C:16]#[C:15][CH2:14][CH2:13][N:17]2[C:21](=[O:22])[C:20]3[C:19](=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:18]2=[O:27])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 11575IodobenzeneHCID 11171619N-(3-Butynyl)phthalimide

Product 1

HCID 12134165HCID 12134165, compoundYield 89.6%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

Under a nitrogen atmosphere, 35 ml of tetrahydrofuran, 3.06 g of iodobenzene, and 9.0 ml of triethylamine were added to 535 mg of dichlorobis(triphenylphosphine)palladium, 145 mg of copper iodide, and 3.00 g of N-(3-butynyl)phthalimide. The obtained mixture was stirred under reflux for 4 hours. After completion of the stirring, the reaction solution was cooled to a room temperature, and a solid was then filtrated. The filtrate was concentrated, and the residue was then purified by column chromatography (Wako Gel C-200; toluene:ethyl acetate=4:1), so as to obtain 3.70 g of a phthalimide compound.

Workup

  1. temperatureunder reflux for 4 hours
  2. filtrationa solid was then filtrated
  3. concentrationThe filtrate was concentrated
  4. customthe residue was then purified by column chromatography (Wako Gel C-200; toluene:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-706a2d360d4b480a9cb86a204c966262
Source dataset
uspto-grants-2013_11
Patent number
US08586505B2

Reaction notes

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