反応 #1049536

反応方程式

4-(5-heptyl-2-pyridyl)-phenol

(8-bromooctyl)-cyclopentane

potassium carbonate

→

5-heptyl-2-[4-(8-cyclopentyl-octyloxy)-phenyl]-pyridine

収率 61.0%

溶媒

dimethylformamide

反応条件

後処理

1. 1
   その他The reaction mixture was partitioned between water and diethyl ether
2. 2
   洗浄The organic phase was washed with water and with saturated sodium chloride solution
3. 3
   乾燥dried over magnesium sulphate
4. 4
   ろ過filtered
5. 5
   濃縮the filtrate was concentrated
6. 6
   その他Chromatography of the crude product (0.28 g) on 10 g of silica gel with hexane/ethyl acetate 37:3 (v/v) and two-fold recrystallization of the product-containing fractions from 3 ml of hexane each time

実験手順

A mixture of 0.157 g of 4-(5-heptyl-2-pyridyl)-phenol, 0.153 g of (8-bromooctyl)-cyclopentane, 6 ml of dimethylformamide and 0.24 g of finely powdered potassium carbonate was stirred at 55° C. for 3 hours. The reaction mixture was partitioned between water and diethyl ether. The organic phase was washed with water and with saturated sodium chloride solution, dried over magnesium sulphate, filtered and the filtrate was concentrated. Chromatography of the crude product (0.28 g) on 10 g of silica gel with hexane/ethyl acetate 37:3 (v/v) and two-fold recrystallization of the product-containing fractions from 3 ml of hexane each time gave 0.16 g of pure 5-heptyl-2-[4-(8-cyclopentyl-octyloxy)-phenyl]-pyridine; m.p. (C-SI) 38.3° C., SI -SC 56.9° C., cl.p. (SC -I) 72.6° C.

出典