p-Diiodobenzene → (E)(E) 5-[4-(5-hydroxy-pent-3-en-1-ynyl)-phenyl]-pent-2-en-4-yn-1-ol

HRID 1353182Notes

Reaction equation

HRID 1353182 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[CH2:9]([OH:14])[CH:10]=[CH:11][C:12]#[CH:13]>C(NC(C)C)(C)C.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:14][CH2:9]/[CH:10]=[CH:11]/[C:12]#[C:13][C:2]1[CH:7]=[CH:6][C:5]([C:13]#[C:12]/[CH:11]=[CH:10]/[CH2:9][OH:14])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 12208p-DiiodobenzeneHCID 977582-Penten-4-yn-1-ol

Product 1

HCID 11299391(E)(E) 5-[4-(5-hydroxy-pent-3-en-1-ynyl)-phenyl]-pent-2-en-4-yn-1-olYield 55%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 7912DiisopropylamineSolvent2×

Procedure

To a solution of 1,4-diiodobenzene (1.32 g, 4.0 mmol) in diisopropylamine (12 mL) under a nitrogen atmosphere were added copper(I) iodide (60 mg, 0.3 mmol) and tetrakis(triphenylphosphine)palladium (80 mg, 0.07 mmol). After the mixture stirred for 1 h, a solution of 2-penten-4-yn-1-ol (1.0 g, 12.0 mmol) in diisopropylamine (7 mL) was added. After stirring under a nitrogen at 60° C. for 8 h, the reaction mixture was filtered and the filtrate evaporated to dryness. The product was purified by flash chromatography using toluene/ethyl acetate (2:1) graduated to ethyl acetate as eluent to give 520 mg (55%) of (E)(E) 5-[4-(5-hydroxy-pent-3-en-1-ynyl)-phenyl]-pent-2-en-4-yn-1-ol.

Workup

  1. stirringAfter stirring under a nitrogen at 60° C. for 8 h
  2. filtrationthe reaction mixture was filtered
  3. customthe filtrate evaporated to dryness
  4. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-629ded98a4074034b49405b17274cf59
Source dataset
uspto-grants-2007_05
Patent number
US07220877B2

Reaction notes

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