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

HRID 1662158ノート

反応式

HRID 1662158 の反応式
[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]=1

参加物

5

反応物 2

HCID 135942-Cyclohexen-1-oneHCID 27343894-(Trifluoromethyl)phenylboronic acid

生成物 1

HCID 11436439(R)-3-(4-(trifluoromethyl)phenyl)cyclohexanone

試薬・触媒・溶媒 2

HCID 11010647ethene;(Z)-4-hydroxypent-3-en-2-one;rhodium触媒HCID 218864351,4-Dioxane--water (1/1)溶媒

反応条件

温度
100 °C

実験手順

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=10 (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)+.

後処理

  1. customThe material was transferred to a separatory funnel
  2. extractionextracted with ethyl acetate (150 mL)
  3. washThe resulting organic layer was washed with NaHCO3 (75 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe mixture was purified on SiO2 (hexane/ethyl acetate 4/1)

出典と根拠

ORDレコード
ord-1c06f8f3fb814c59911b62ca7dc8a1fd
出典データセット
uspto-grants-2011_10
特許番号
US08030504B2

反応ノート

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