Ethyl 4-ethynylbenzoate → HCID 56987556, compound

HRID 963010Notes

Reaction equation

HRID 963010 reaction equation
I[CH:2]=[CH:3][C:4]1[C:5](=[O:11])[CH2:6][CH2:7][CH2:8][C:9]=1[CH3:10].[C:12]([C:14]1[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=1)#[CH:13]>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.[Cu]I.C(N(CC)CC)C>[CH3:10][C:9]1[CH2:8][CH2:7][CH2:6][C:5](=[O:11])[C:4]=1[CH:3]=[CH:2][C:13]#[C:12][C:14]1[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=1

Participants

6

Reactant 2

HCID 15540683Ethyl 4-ethynylbenzoateHCID 57287130HCID 57287130, compound2×

Product 1

HCID 56987556HCID 56987556, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 2-(2-iodoethenyl)-3-methyl-2-cyclohexen-1-one (Compound 4, 1.74 g, 6.64 mmol), ethyl 4-ethynylbenzoate (1.73 g, 9.96 mmol) and triethylamine (80 mL) was purged with argon for 10 minutes, and then treated with bis(triphenylphosphine)palladium (II) chloride (23 mg, 0.03 mmol) and copper (I) iodide (6.3 mg, 0.03 mmol). The solution was stirred 40° C. for 3 hours, and concentrated under the vacuum of a water aspirator. The residue was dissolved in ethyl acetate and washed with saturated aqueous NH4Cl. The layers were separated and the aqueous layer was extracted 2× with ethyl acetate. The combined organic fractions were washed with water, and brine, and dried (MgSO4). The solvents were removed under reduced pressure, and the residue was purified by silica gel chromatography (88:12, hexane:ethyl acetate) to give the title compound as a yellow crystaline solid.

Workup

  1. concentrationconcentrated under the vacuum of a water aspirator
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with saturated aqueous NH4Cl
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted 2× with ethyl acetate
  6. washThe combined organic fractions were washed with water, and brine
  7. dry with materialdried (MgSO4)
  8. customThe solvents were removed under reduced pressure
  9. customthe residue was purified by silica gel chromatography (88:12, hexane:ethyl acetate)

Sources & evidence

ORD record
ord-6d82e1a984894aa6becf26afdc725f8c
Source dataset
uspto-grants-1998_06
Patent number
US05760276

Reaction notes

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