Potassium Carbonate → 2-Cyclohexen-1-one, 3-phenyl-

HRID 1675499Notes

Reaction equation

HRID 1675499 reaction equation
Br[C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([O-])([O-])=O.[K+].[K+]>[Pd].C(O)C>[C:9]1([C:2]2[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 109650383-Bromocyclohex-2-enone

Product 1

HCID 825672-Cyclohexen-1-one, 3-phenyl-Yield 75.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

A microwave vial was charged with a stir bar, 3-bromocyclohex-2-enone (65 mg, 1 equiv., 0.37 mmol), phenyl boronic acid (55 mg, 1.2 equiv., 0.45 mmol) and ethanol (4 mL). To the solution was added 1M K2CO3 (1.2 equiv., 0.45 mmol) followed by the addition of the polymer supported palladium FC 1001 (27 mg, 3 mol % Pd) catalyst. The reaction was subjected to the following microwave conditions: Power 250 W, Temperature 110° C., ramp time 1:00 min, time holds 5 min, Power Max on (continuous air cooling). The reaction was then cooled to room temperature and filtered through a plug of celite eluding with ethyl acetate. The solvent was evaporated on a rotary evaporator. The residue was diluted in methylene chloride and washed with brine. The organic layers were dried over MgSO4 and the residue was purified by automated silica gel chromatography using gradient elution (0 to 20% ethyl acetate/hexanes) affording the desired product as a white solid (48 mg, 75% yield). 1H NMR (300 MHz, CDCl3): δ 7.50-7.53 (m, 2H), 7.36-7.41 (m, 3H), 6.40 (t, J=1.4 Hz, 1H), 2.76 (td, J=6.9, 1.2 Hz, 2H), 2.48 (t, J=6.9 Hz, 2H), 2.14 (quintet, J=6.9 Hz, 2H). 13C (75 MHz, CDCl3): 199.6, 159.6, 138.6, 129.8, 128.6, 125.9, 125.3, 37.3, 28.1, 22.9. LCMS (ESI): mass calcd for (C12H12O) m/z 172.09; measured [M+H]+: m/z 173.17.

Workup

  1. additionA microwave vial was charged with a stir bar
  2. additionfollowed by the addition of the polymer
  3. temperaturePower Max on (continuous air cooling)
  4. filtrationfiltered through a plug of celite eluding with ethyl acetate
  5. customThe solvent was evaporated on a rotary evaporator
  6. additionThe residue was diluted in methylene chloride
  7. washwashed with brine
  8. dry with materialThe organic layers were dried over MgSO4
  9. customthe residue was purified by automated silica gel chromatography
  10. washelution (0 to 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-5d99f7456f9641098f93680d9f22e77e
Source dataset
uspto-grants-2011_08
Patent number
US08003692B2

Reaction notes

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