5-Phenyl-1-pentyne → 4-(5-Phenylpent-1-ynyl)thiophen-2-carboxaldehyde

HRID 1063444Notes

Reaction equation

HRID 1063444 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]#[CH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:13]1[CH:14]=[C:15]([CH:18]=[O:19])[S:16][CH:17]=1>O1CCCC1.[Cu]I.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.C(N(CC)CC)C>[C:1]1([CH2:7][CH2:8][CH2:9][C:10]#[C:11][C:13]2[CH:14]=[C:15]([CH:18]=[O:19])[S:16][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 2

HCID 745735-Phenyl-1-pentyneHCID 877924-Bromothiophene-2-carbaldehyde

Product 1

HCID 222799374-(5-Phenylpent-1-ynyl)thiophen-2-carboxaldehydeYield 78%

Reagents, catalysts & solvents 4

HCID 8471TriethylamineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

5-Phenylpent-1-yne (18.1 g, 126 mmol) was dissolved in tetrahydrofuran (100 ml), and then 4-bromothiophen-2-carboxaldehyde (18.7 g, 98 mmol) in tetrahydrofuran (200 ml), triethylamine (150 ml, 1.07 mmol), copper(I) iodide (962 mg, 5.05 mmol), and dichlorobis(triphenylphosphine)palladium (3.54 g, 5.04 mmol) were added thereto, and the mixture was stirred at 50° C. for 4 hours under a nitrogen atmosphere. After the reaction solution was filtered, the filtrate was evaporated under reduced pressure. To the residue was added ether, and the solution was washed with water and a saturated aqueous sodium chloride solution, respectively. After the ether layer was dried over anhydrous sodium sulfate, the solvent was evaporated in vacuo. The residue was purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=100:1-10:1) to afford the title compound (19.4 g, 78% yield).

Workup

  1. filtrationAfter the reaction solution was filtered
  2. customthe filtrate was evaporated under reduced pressure
  3. additionTo the residue was added ether
  4. washthe solution was washed with water
  5. dry with materialAfter the ether layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=100:1-10:1)

Sources & evidence

ORD record
ord-c065138a2ae9487c8699a1ce693ca3f4
Source dataset
uspto-grants-2005_11
Patent number
US06964976B2

Reaction notes

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