2-Cyclohexen-1-one → (R)-3-(4-(trifluoromethyl)phenyl)cyclohexanone
Reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[F:8][C:9]([F:20])([F:19])[C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1>C/C(/O)=C/C(C)=O.C=C.C=C.[Rh].O1CCOCC1.O>[F:8][C:9]([F:20])([F:19])[C:10]1[CH:15]=[CH:14][C:13]([C@@H:3]2[CH2:4][CH2:5][CH2:6][C:1](=[O:7])[CH2:2]2)=[CH:12][CH:11]=1Participants
Conditions
- Temperature
- 100 °C
Procedure
To a 40 ml microwave flask containing dioxane/H2O (10/1) (22 mL) was added cyclohexen-1-one (1.35 g, 14.0 mmol), acetylacetonatobis(ethylene)rhodium(I) (0.36 g, 1.40 mmol), R-2,2′-bis(diphenyl-phosphino)-1,1′-binaphthyl (0.88 g, 1.40 mmol) and 4-(trifluoromethyl)-phenylboronic acid (5.0 g, 28.0 mmol). The mixture was heated in the microwave (Personal Chemistry) at 100° C. for 20 minutes. The material was transferred to a separatory funnel and extracted with ethyl acetate (150 mL). The resulting organic layer was washed with NaHCO3 (75 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The mixture was purified on SiO2 (hexane/ethyl acetate 4/1) to provide the title compound. [α]D=+13.62 c=1.0 (CH3OH). 1H NMR (CD3OD, 300 MHz); δ 1.72-2.20 (m, 5H), 2.35-2.73 (m, 3H), 3.06-3.15 (m, 1H), 7.40-7.42 (m, 2H), 7.46-7.63 (m, 2H). MS (+ESI)m/z 242 (M+NH4—H2O)+.
Workup
- customThe material was transferred to a separatory funnel
- extractionextracted with ethyl acetate (150 mL)
- washThe resulting organic layer was washed with NaHCO3 (75 mL)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe mixture was purified on SiO2 (hexane/ethyl acetate 4/1)
Sources & evidence
- ORD record
- ord-ff4df05dbf824a36b97aab878fb1b73d
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08350083B2
Reaction notes
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