Reaktion #95270

Reaktionsgleichung

ammonium chloride

butyllithium

1-pentyne

β-chloropropionaldehyde

→

1-chloro-3-hydroxy-4-octyne

Lösungsmittel

hexane

hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThe resulting white sludge is diluted with 20 ml
2. 2
   Sonstigebrought to 10° C.
3. 3
   workup.ADDITIONtreated with 11 g
4. 4
   workup.STIRRINGto stir at ambient temperature for 18 hours
5. 5
   SonstigeThe organic phase is separated
6. 6
   Waschenwashed
7. 7
   workup.ADDITIONwith dilute hydrochloric solution
8. 8
   Trocknendried with anhydrous magnesium sulfate
9. 9
   workup.DISTILLATIONDistillation
10. 10
    Sonstigegives 5.1 g

Vorschrift

To 68 ml. of 1.6 M butyllithium in hexane at -50° C. is added dropwise, with stirring, 7.4 g. of 1-pentyne. The resulting white sludge is diluted with 20 ml. of hexane, brought to 10° C. and treated with 11 g. of freshly prepared β-chloropropionaldehyde (Org. Syn., Coll. Vol. I, p. 166) at such a rate that the temperature is maintained at 10°-15° C. The solution is allowed to stir at ambient temperature for 18 hours then treated with saturated ammonium chloride solution. The organic phase is separated, washed with dilute hydrochloric solution, dried with anhydrous magnesium sulfate and taken to dryness. Distillation gives 5.1 g. of product b.p. 65°-66° C. at 0.3 nm.; λmax. 2.95 (--OH) and 4.55μ (--C≡C--); vapor phase chromatography shows one peak.

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