Cyclopentene → HCID 58566800, compound

HRID 2069693Notes

Reaction equation

HRID 2069693 reaction equation
I[C:2]1[CH:3]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]=2[CH:12]=1.[CH:18]1[CH2:22][CH2:21][CH2:20][CH:19]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C([O-])([O-])=O.[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CCOC(C)=O.CN(C=O)C>[CH:22]1([C:2]2[CH:3]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]3[O:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]=3[CH:12]=2)[CH2:21][CH2:20][CH:19]=[CH:18]1

Participants

9

Reactant 4

HCID 8882CyclopenteneHCID 11430Potassium CarbonateHCID 2724141Tetrabutylammonium FluorideHCID 58566704HCID 58566704, compound

Product 1

HCID 58566800HCID 58566800, compoundYield 66.4%

Reagents, catalysts & solvents 4

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

In a 20-mL microwave-tube was added ethyl 5-iodo-2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylate (0.692 g, 2.0 mol), cyclopentene (0.882 mL, 10.0 mol), TBAF (0.644 g, 2.0 mol), K2CO3 (0.691 g, 5.0 mol), DMF (8.0 mL), palladium (II) acetate (0.011 g, 0.05 mmol), and tri-o-tolyphosphine (0.030 g, 0.10 mmol) under N2. The mixture was sealed in the glass tube and was stirred at 110° C. overnight (21 hours). The reaction was cooled to room temperature and EtOAc (10 mL) was added. The mixture was stirred for 30 minutes, filtered through celite and rinsed with EtOAc (3×5 mL). The organic layer was washed with water (2×10 mL), brine (10 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography (0-10% EtOAc in hexanes) to provide the desired ethyl 5-(cyclopent-2-en-1-yl)-2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylate (873B) (0.380 g, 66.4%) as a yellow oil.

Workup

  1. customThe mixture was sealed in the glass tube
  2. temperatureThe reaction was cooled to room temperature
  3. stirringThe mixture was stirred for 30 minutes
  4. filtrationfiltered through celite
  5. washrinsed with EtOAc (3×5 mL)
  6. washThe organic layer was washed with water (2×10 mL), brine (10 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by chromatography (0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-02a3adfc521b4e1ebcc339e3c64ed7f1
Source dataset
uspto-grants-2012_10
Patent number
US08299117B2

Reaction notes

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