2-Cyclohexen-1-one → 3-Phenylcyclohexanone

HRID 510753ノート

反応式

HRID 510753 の反応式
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CCOCC1.O.[C:17]1(=[O:23])[CH2:22][CH2:21][CH2:20][CH:19]=[CH:18]1>CCOC(C)=O.C/C(/O)=C/C(C)=O.C=C.C=C.[Rh].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]1([CH:19]2[CH2:20][CH2:21][CH2:22][C:17](=[O:23])[CH2:18]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

7

反応物 3

HCID 135942-Cyclohexen-1-oneHCID 66827Phenylboronic AcidHCID 218864351,4-Dioxane--water (1/1)

生成物 1

HCID 2736613-Phenylcyclohexanone収率 33.4%

試薬・触媒・溶媒 3

HCID 634876Binap, (A+-)-触媒HCID 11010647ethene;(Z)-4-hydroxypent-3-en-2-one;rhodium触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

To a solution of phenylboronic acid (0.630 g, 5.17 mmol) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.0193 g, 0.0310 mmol) in 10:1 dioxane/water (2.5 ml) was added acetylacetonatobis(ethylene)rhodium(I) (0.00800 g, 0.0310 mmol), and the reaction was degassed with argon. To this was added cyclohex-2-enone (0.100 ml, 1.03 mmol), and the reaction was heated to 120° C. for 16 hours in a screw-top vial. The reaction was allowed to cool to ambient temperature, diluted with EtOAc, and washed with twice with saturated sodium bicarbonate and once with saturated sodium chloride. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude material was purified on a Biotage SP1 system eluting with a linear gradient of 5-50% EtOAc in hexanes to yield 60 mg of the title compound (33.3% yield).

後処理

  1. customthe reaction was degassed with argon
  2. temperatureto cool to ambient temperature
  3. washwashed with twice with saturated sodium bicarbonate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified on a Biotage SP1 system
  8. washeluting with a linear gradient of 5-50% EtOAc in hexanes

出典と根拠

ORDレコード
ord-05daa2d1e389475396f709d815df3669
出典データセット
uspto-grants-2015_08
特許番号
US09096567B2

反応ノート

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