Reaktion #95554

Reaktionsgleichung

1,1-Dimethoxy-6-iodohexane

acetylene

→

1,1-dimethoxy-oct-7-yne

Ausbeute 96.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAcetylene was bubbled through ca. 300 ml of liquid ammonia while 8.1 g (0.35 atom) of sodium
2. 2
   workup.ADDITIONwas added in small pieces
3. 3
   workup.ADDITIONAfter the disappearance of the blue color, dimethylsulfoxide (150 ml) was added cautiously
4. 4
   Sonstigewas bubbled through the stirred mixture
5. 5
   Sonstigeto evaporate
6. 6
   Sonstigehad reached 0°
7. 7
   workup.ADDITIONdilute NH4Cl solution was added
8. 8
   SonstigeThe organic layer was separated
9. 9
   Waschenwashed with water
10. 10
    Trocknendried (Na2SO4)
11. 11
    Sonstigeevaporated
12. 12
    workup.DISTILLATIONDistillation of the residue

Vorschrift

Acetylene was bubbled through ca. 300 ml of liquid ammonia while 8.1 g (0.35 atom) of sodium was added in small pieces. After the disappearance of the blue color, dimethylsulfoxide (150 ml) was added cautiously. 1,1-Dimethoxy-6-iodohexane (8.16 g; 0.3 Mole) was then added over a period of 10 min. while acetylene was bubbled through the stirred mixture. The ammonia was allowed to evaporate and was replaced with ether. When the mixture had reached 0°, dilute NH4Cl solution was added. The organic layer was separated, washed with water, dried (Na2SO4), and evaporated. Distillation of the residue gave 48.9 g (96%) of 1,1-dimethoxy-oct-7-yne, b.p. 91°/8 Torr.

Quelle