反応 #11572

反応方程式

diethylzinc

hexane

chloroiodomethane

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

ammonium chloride

ammonium chloride

→

titled compound

収率 3.5%

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

収率 3.5%

溶媒

1,2-dichloroethane

ethyl acetate

反応条件

後処理

1. 1
   温度ice-cooling
2. 2
   温度cooling
3. 3
   workup.STIRRINGthe whole was stirred at room temperature for 20 minutes
4. 4
   洗浄The organic layer was washed with a saturated aqueous sodium chloride solution (10 ml)
5. 5
   乾燥dried over anhydrous magnesium sulfate
6. 6
   その他The solvent was evaporated under reduced pressure
7. 7
   その他the resulting residue was purified by silica gel column chromatography

実験手順

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.

出典