Reaktion #2163093

Reaktionsgleichung

diethylzinc

hexane

chloroiodomethane

(Z)-1-[2-(1-adamantyl)ethyl]-1-pentyl-3-[3-(4-pyridyl)-2-propenyl]urea

ammonium chloride

ammonium chloride

→

titled compound

Ausbeute 3.5%

cis 1-[2-(1-Adamantyl)ethyl]-1-pentyl-3-[2-(4-pyridyl)cyclopropylmethyl]urea

Ausbeute 3.5%

Lösungsmittel

1,2-dichloroethane

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturice-cooling
2. 2
   Temperaturcooling
3. 3
   workup.STIRRINGthe whole was stirred at room temperature for 20 minutes
4. 4
   WaschenThe organic layer was washed with a saturated aqueous sodium chloride solution (10 ml)
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   SonstigeThe solvent was evaporated under reduced pressure
7. 7
   Sonstigethe resulting residue was purified by silica gel column chromatography

Vorschrift

A 1.0 M solution of diethylzinc in hexane (3.1 ml, 3.1 mmol) and chloroiodomethane (0.44 ml, 6.1 mol) were added to a solution of (Z)-1-[2-(1-adamantyl)ethyl]-1-pentyl-3-[3-(4-pyridyl)-2-propenyl]urea (Compound No. 1-111) in anhydrous 1,2-dichloroethane (3 ml) under a nitrogen atmosphere and ice-cooling, and the mixture was stirred for one hour. A saturated aqueous ammonium chloride solution (10 ml) was added to the reaction mixture under ice-cooling, and the whole was stirred at room temperature for 20 minutes and distributed with ethyl acetate (20 ml) and a saturated aqueous ammonium chloride solution (10 ml). The organic layer was washed with a saturated aqueous sodium chloride solution (10 ml) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give 9.0 mg (3.5%) of the titled compound as colorless crystals.

Quelle