반응 #1476811

반응 방정식

5-chloropentanol

2-furyllithium

n-butyllithium

furan

ammonium chloride

→

5-chloro-1-(2-furyl)-1-pentanol

용매

ether

ether

hexane

CH2Cl2

반응 조건

후처리

1. 1
   온도The mixture is warmed to 0° during 20 minutes
2. 2
   세척The ether phase is washed with water and brine
3. 3
   건조dried over magnesium sulfate and potassium carbonate mixture
4. 4
   농축concentrated
5. 5
   기타to give a liquid, pmr spectrum (CDCl3)

실험 절차

To a stirred suspension of 2-furyllithium (prepared from 0.53 moles of n-butyllithium and 39.5 g of furan by the procedure of J. Org. Chem., 27, 1216 (1962)) in 350 ml of ether and ca. 200 ml of hexane at -78° is added a solution of 57.9 g of 5-chloropentanol (Chem. Abstr., 59, 7579F (1963)) in 80 ml of ether during 25 minutes. The mixture is warmed to 0° during 20 minutes, stirred at 0° for 15 minutes, and treated with 140 ml of saturated ammonium chloride. The ether phase is washed with water and brine, dried over magnesium sulfate and potassium carbonate mixture, and concentrated to give a liquid, pmr spectrum (CDCl3): δ3.59 (triplet, CH2Cl2) and 4.70 (triplet, CH2CHOH).

출처