Cyclopentylacetylene → Methyl 4-(cyclopentylethynyl)-2-methylbenzoate

HRID 2102918Notes

Reaction equation

HRID 2102918 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:12])[CH:3]=1.[C:13]([CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)#[CH:14]>C(N(CC)CC)C.[Cu](I)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>[CH:15]1([C:13]#[C:14][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:12])[CH:3]=2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 2

HCID 136725CyclopentylacetyleneHCID 22031226Methyl 4-bromo-2-methylbenzoate

Product 1

HCID 57804197Methyl 4-(cyclopentylethynyl)-2-methylbenzoate

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 4-bromo-2-methylbenzoate (1.0 g, 4.4 mmol) was dissolved in triethylamine (5 mL). To the mixture was added copper iodide (43 mg, 5 mol %), followed by PdCl2(PPh3)2 (157 mg, 5 mol %) and ethynylcyclopentane (0.75 mL, 5.3 mmol). The mixture was heated in a sealed pressure tube at 80° C. for 3 hours. After completion of the reaction, the triethylamine was evaporated and the residue was dissolved in EtOAc and filtered through Celite®. The organic layer was washed with water, brine, and dried (Na2SO4), then filtered and concentrated under vacuum. The residue was purified by column chromatography on sililca gel using EtOAc-hexane (0-100% gradient) as eluet to give the desired product.

Workup

  1. customAfter completion of the reaction
  2. customthe triethylamine was evaporated
  3. dissolutionthe residue was dissolved in EtOAc
  4. filtrationfiltered through Celite®
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by column chromatography on sililca gel

Sources & evidence

ORD record
ord-5857646d2e6a4d60b7c85b4128a7d606
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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