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

HRID 1893071Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1893071
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:37]1[CH2:42][CH2:41][CH:40]([CH:43]=[CH2:44])[CH2:39][CH2:38]1)[CH2:33][CH2:34][CH2:35][CH3:36]>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:44]=[CH:43][CH:40]3[CH2:41][CH2:42][CH:37]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:38][CH2:39]3)=[CH:27][CH:26]=2)[CH2:21][CH2:20]1)=[O:18]

Komponenten

7

Edukt 4

HCID 31374DimethylacetamideHCID 62657Potassium Phosphate, TribasicHCID 190391931-Pentyl-4-vinyl-cyclohexaneHCID 584532034-(4-Bromophenyl)cyclohexane carboxylic acid methyl ester

Produkt 1

HCID 584532174-{4-[2-(4-Pentyl-cyclohexyl)-ethenyl]-phenyl}cyclohexane carboxylic acid methyl esterAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

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 8.33 g (40 mmol) of 1-pentyl-4-vinyl-cyclohexane 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 9.8 g (62%) of 4-{4-[2-(4-pentyl-cyclohexyl)-ethenyl]-phenyl}cyclohexane carboxylic acid methyl ester.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-14f5fc01f0c14d63b8ea886b39ed57ed
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08512598B2

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