Hydrochloric Acid → (3RS,4SR)-3-(3,4-dimethoxyphenyl)-4-nitrocyclohexanone

HRID 334350

反応式

HRID 334350 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[N+:11]([O-:13])=[O:12])=[CH:5][C:4]=1[O:14][CH3:15].C[Si](C)(C)[O:18][C:19]([CH:21]=[CH2:22])=[CH2:20].C1(C)C=CC=CC=1.Cl>C(OCC)(=O)C>[CH3:15][O:14][C:4]1[CH:5]=[C:6]([CH:9]2[CH:10]([N+:11]([O-:13])=[O:12])[CH2:22][CH2:21][C:19](=[O:18])[CH2:20]2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 5546572-(Trimethylsiloxy)-1,3-butadieneHCID 7096881,2-Dimethoxy-4-(2-nitrovinyl)benzene

生成物 1

HCID 67022408(3RS,4SR)-3-(3,4-dimethoxyphenyl)-4-nitrocyclohexanone

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
140 °C

実験手順

90.0 g of 3,4-dimethoxy-ω-nitrostyrene (compound G2), 90 ml of 2-trimethylsilyloxy-1,3-butadiene and 180 ml of abs. Toluene are put in an autoclave, where the mixture is stirred at 140° C. for 2 days and then cooled. After addition of 1000 ml of ethyl acetate, 300 ml of a 2 N solution of hydrochloric acid are dropped under stirring. The phases are separated and the aqueous layer is extracted three times with dichloromethane. The combined organic extracts are washed with saturated sodium hydrogencarbonate solution, dried over magnesium sulfate and the solvents are removed under reduced pressure to give 150 g of the crude title compound. Further purification is carried out by chromatography on silica gel using petroleum ether/ethyl acetate in the ratio 1/1 as eluent to give 81.5 g (67% of theory) of the pure title compound.

後処理

  1. temperaturecooled
  2. additionare dropped
  3. stirringunder stirring
  4. customThe phases are separated
  5. extractionthe aqueous layer is extracted three times with dichloromethane
  6. washThe combined organic extracts are washed with saturated sodium hydrogencarbonate solution
  7. dry with materialdried over magnesium sulfate
  8. customthe solvents are removed under reduced pressure
  9. customto give 150 g of the crude title compound
  10. customFurther purification

出典と根拠

ORDレコード
ord-0a87d376fae54e52ab8e2976813d04d4
出典データセット
uspto-grants-2014_11
特許番号
US08883818B2

関連ノート

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