반응 #95270

반응 방정식

ammonium chloride

butyllithium

1-pentyne

β-chloropropionaldehyde

→

1-chloro-3-hydroxy-4-octyne

용매

hexane

hexane

반응 조건

후처리

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

실험 절차

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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