Reaktion #94689

Reaktionsgleichung

5-chloropentanol

2-furyllithium

n-butyllithium

furan

ammonium chloride

→

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

Lösungsmittel

hexane

ether

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONtreated with 140 ml
2. 2
   WaschenThe ether phase is washed with water and brine
3. 3
   Trocknendried over magnesium sulfate and potassium carbonate mixture
4. 4
   Einengenconcentrated
5. 5
   Sonstigeto give a liquid, pmr spectrum (CDCl3) δ 3.59 (triplet, CH2Cl) and 4.70 (triplet, CH2CHOH)

Vorschrift

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 with 200 ml. of hexane at -78° C 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 mixtures is warmed to 0° C. during 20 minutes, stirred at 0° C 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) δ 3.59 (triplet, CH2Cl) and 4.70 (triplet, CH2CHOH).

Quelle