2-Cyclohexen-1-one → 3-(4-(Benzyloxy)phenyl)cyclohexanone

HRID 1713844Notes

Reaction equation

HRID 1713844 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[C:64]1(=[O:70])[CH2:69][CH2:68][CH2:67][CH:66]=[CH:65]1.C(=O)([O-])O.[Na+]>O1CCOCC1.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:66]2[CH2:67][CH2:68][CH2:69][C:64](=[O:70])[CH2:65]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 135942-Cyclohexen-1-oneHCID 516892Sodium BicarbonateHCID 634876Binap, (A+-)-HCID 27343144-Benzyloxy-phenylboronic acid

Product 1

HCID 594642333-(4-(Benzyloxy)phenyl)cyclohexanoneYield 23%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

[4-(Benzyloxy)phenyl]boronic acid (2 g, 8.77 mmol) was dissolved in dioxane/water (50 mL/5 mL) and Rh(acac)(C2H4)2 (68 mg, 0.26 mmol) and racemic BINAP (164 mg, 0.26 mmol) were added. The mixture was degassed 3 times and put under a nitrogen atmosphere. Cyclohexenone (1.02 mL, 10.52 mmol) was added to the yellow solution and the mixture heated at reflux overnight. The reaction mixture was cooled, saturated aqueous sodium hydrogen carbonate solution (50 mL) added, then extracted with EtOAc (2×100 mL). The organic extracts were washed with water (100 mL) and dried. Volatile material was removed by evaporation and purification by chromatography gave the title compound (565 mg, 23%) as a solid; 1H NMR δ1.65-1.69 (1H, m), 1.78-1.93 (2H, m), 1.99-2.04 (1H, m), 2.22-2.35 (2H, m), 2.39-2.43 (1H, m), 2.65 (1H, m), 2.90-2.96 (1H, m), 5.08 (2H, s), 6.96 (2H, d), 7.20 (2H, d), 7.31-7.45 (5H, m); MS m/e MH+ 281.

Workup

  1. customThe mixture was degassed 3 times
  2. temperaturethe mixture heated
  3. temperatureat reflux overnight
  4. temperatureThe reaction mixture was cooled
  5. extractionextracted with EtOAc (2×100 mL)
  6. washThe organic extracts were washed with water (100 mL)
  7. customdried
  8. customVolatile material was removed by evaporation and purification by chromatography

Sources & evidence

ORD record
ord-cfe364af517443f5b927cf917a5caa00
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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