Dimethylacetamide → 4-{4-[2-(4-Propyl-cyclohexyl)-ethenyl]-phenyl}cyclohexane carboxylic acid methyl ester

HRID 1893069ノート

反応式

HRID 1893069 の反応式
CN(C)C(=O)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:15][O:16][C:17]([CH:19]1[CH2:24][CH2:23][CH:22]([C:25]2[CH:30]=[CH:29][C:28](Br)=[CH:27][CH:26]=2)[CH2:21][CH2:20]1)=[O:18].[CH2:32]([CH:35]1[CH2:40][CH2:39][CH:38]([CH:41]=[CH2:42])[CH2:37][CH2:36]1)[CH2:33][CH3:34]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:15][O:16][C:17]([CH:19]1[CH2:24][CH2:23][CH:22]([C:25]2[CH:30]=[CH:29][C:28]([CH:42]=[CH:41][CH:38]3[CH2:39][CH2:40][CH:35]([CH2:32][CH2:33][CH3:34])[CH2:36][CH2:37]3)=[CH:27][CH:26]=2)[CH2:21][CH2:20]1)=[O:18]

参加物

7

反応物 4

HCID 31374DimethylacetamideHCID 62657Potassium Phosphate, TribasicHCID 534183861-Ethenyl-4-propylcyclohexaneHCID 584532034-(4-Bromophenyl)cyclohexane carboxylic acid methyl ester

生成物 1

HCID 584532244-{4-[2-(4-Propyl-cyclohexyl)-ethenyl]-phenyl}cyclohexane carboxylic acid methyl ester収率 60%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒

実験手順

180 mL of N,N-dimethylacetamide (DMA) solution including 12.8 g (60.1 mmol) of potassium phosphate, 14.3 g (48 mmol) of 4-(4-bromophenyl)cyclohexanecarboxylic acid methyl ester produced in Example 1-1, and 6.09 g (40 mmol) of 1-propyl-4-vinylcyclohexane was poured to flask filled with Argon gas. Then, 0.17 g (catalytic amount) of palladium acetate was added to the flask and reacted in oil bath at 120° C. for 32 hours. After reaction, 100 mL of distilled water was added to the reaction mixture, extracted by ethyl acetate, and then the aqueous layer was extracted by chloroform. The organic layer was dried by Na2SO4, concentrated under reduced pressure, and then recrystallized from ethanol to obtain 8.8 g (60%) of 4-{4-[2-(4-propyl-cyclohexyl)-ethenyl]-phenyl}cyclohexane carboxylic acid methyl ester.

後処理

  1. additionwas poured to flask
  2. additionfilled with Argon gas
  3. customreacted in oil bath at 120° C. for 32 hours
  4. additionwas added to the reaction mixture
  5. extractionextracted by ethyl acetate
  6. extractionthe aqueous layer was extracted by chloroform
  7. dry with materialThe organic layer was dried by Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customrecrystallized from ethanol

出典と根拠

ORDレコード
ord-34bf4b2efda845679bb6f9bbc22e9307
出典データセット
uspto-grants-2013_08
特許番号
US08512598B2

反応ノート

読み込み中…