2-Cyclopenten-1-one → HCID 64522109, compound

HRID 1624030Notes

Reaction equation

HRID 1624030 reaction equation
[F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][C:7]=1[F:8].[C:12]1(=[O:17])[CH2:16][CH2:15][CH:14]=[CH:13]1.[Sb](Cl)(Cl)Cl.C([O-])(=O)C.[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:14]2[CH2:15][CH2:16][C:12](=[O:17])[CH2:13]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

7

Reactant 4

HCID 135882-Cyclopenten-1-oneHCID 24814Antimony trichlorideHCID 517045Sodium AcetateHCID 27343373,4-Difluorobenzeneboronic acid

Product 1

HCID 64522109HCID 64522109, compoundYield 58.6%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 176Acetic AcidSolvent

Procedure

To 3,4-difluorophenylboronic acid (9.47 g, 60 mmol), cyclopent-2-enone (4.93 g, 60 mmol), antimony trichloride (1.37 g, 6 mmol), sodium acetate, (9.84 g, 120 mmol) and palladium acetate (1.35 g, 6 mmol) are added to acetic acid (300 mL) under an argon atmosphere. The reaction is stirred at room temperature overnight. The reaction mixture is filtered and poured into water. The material is extracted with ethyl acetate (3×), washed with saturated sodium bicarbonate (3×), brine (3×), dried with sodium sulfate, filtered, and concentrated in vacuo. The material is purified using silica gel chromatography eluting with 10% ethyl acetate in pet ether to give the title compound as a yellow oil (6.9 g, 58%). 1H NMR (300 MHz, CDCl3) δ 7.14-6.95 (m, 3H), 3.41-3.37 (m, 1H), 2.64-2.61 (m, 1H), 2.46-2.23 (m, 4H), 1.93-1.84 (m, 1H).

Workup

  1. filtrationThe reaction mixture is filtered
  2. additionpoured into water
  3. extractionThe material is extracted with ethyl acetate (3×)
  4. washwashed with saturated sodium bicarbonate (3×), brine (3×)
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe material is purified
  9. washeluting with 10% ethyl acetate in pet ether

Sources & evidence

ORD record
ord-e911297c107f4c9ca0041afc0592502f
Source dataset
uspto-grants-2014_07
Patent number
US08778984B2

Reaction notes

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