1,2-Dimethoxyethane → (E)-1-(prop-1-enyl)-4-(3-propylcyclopentyl)cyclohexane

HRID 1464846Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1464846
CO[CH2:3][CH2:4]OC.C(S(C1N(C2C=CC=CC=2)N=NN=1)(=O)=O)C.[CH2:23]([CH:26]1[CH2:30][CH2:29][CH:28]([CH:31]2[CH2:36][CH2:35][CH:34]([CH:37]=O)[CH2:33][CH2:32]2)[CH2:27]1)[CH2:24][CH3:25].C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C1COCC1>[CH:37](/[CH:34]1[CH2:35][CH2:36][CH:31]([CH:28]2[CH2:29][CH2:30][CH:26]([CH2:23][CH2:24][CH3:25])[CH2:27]2)[CH2:32][CH2:33]1)=[CH:3]\[CH3:4]

Komponenten

6

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 7536625-Ethylsulfonyl-1-phenyl-1H-tetrazoleHCID 3251421Potassium bis(trimethylsilyl)amide2×HCID 866602914-(3-Propylcyclopentyl)cyclohexanecarboaldehyde

Produkt 1

HCID 58555698(E)-1-(prop-1-enyl)-4-(3-propylcyclopentyl)cyclohexane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

DME (1,2-dimethoxyethane; 80 ml) and 5-(ethylsulfonyl)-1-phenyl-1H-tetrazole (4.62 g) were added to 4-(3-propylcyclopentyl)cyclohexanecarboaldehyde (3.29 g) obtained in the second step in Example 3, in a reaction vessel under an atmosphere of nitrogen, and the mixture was cooled to −70° C., and then KHMDS (Potassium Hexamethyldisilazide; 20%, in a THF solution) (23.9 ml) was added dropwise. The reaction solution was warmed to room temperature, and was extracted with diethyl ether after the addition of water (50 ml) The resulting organic layer was washed with water and dried over anhydrous sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate/n-heptane=1/9 by volume) and then purified by means of a preparative HPLC system, Model PLC-561 made by GL Sciences Inc. to give (E)-1-(prop-1-enyl)-4-(3-propylcyclopentyl)cyclohexane (2.0 g).

Aufarbeitung

  1. customobtained in the second step in Example 3, in a reaction vessel under an atmosphere of nitrogen
  2. temperatureThe reaction solution was warmed to room temperature
  3. extractionwas extracted with diethyl ether
  4. additionafter the addition of water (50 ml) The resulting organic layer
  5. washwas washed with water
  6. dry with materialdried over anhydrous sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel chromatography (eluent: ethyl acetate/n-heptane=1/9 by volume)
  9. custompurified by means of a preparative HPLC system, Model PLC-561

Quellen und Nachweise

ORD-Eintrag
ord-7aad8b93a92c41659e2b841cf9bacfb5
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999197B2

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