반응 #216451

반응 방정식

Boron trifluoride etherate

1-cyano-1-(3-propyloxetan-3-yl)methyl hex-5-ynoate

Triethylamine

→

1-(Pent-4-ynyl)-4-propyl-2,6,7-trioxabicyclo[2.2.2]octane-3-carbonitrile

용매

dichloromethane

반응 조건

후처리

1. 1
   기타the solvent was removed under vacuum
2. 2
   기타The residue was partitioned between water and diethyl ether
3. 3
   기타The organic phase was separated
4. 4
   세척washed with water and brine
5. 5
   건조before drying over anhydrous magnesium sulphate and evaporation in vacuo
6. 6
   기타The residue was purified by column chromatography on alumina eluting with 1:4 dichloromethane

실험 절차

Boron trifluoride etherate (0.25 ml) was added to a solution of 1-cyano-1-(3-propyloxetan-3-yl)methyl hex-5-ynoate (0.5 g) in dry dichloromethane (10 ml) stirred at -70° under a nitrogen atmosphere. The resulting solution was allowed to warm to room temperature overnight. Triethylamine (0.38 ml.) was added and the solvent was removed under vacuum. The residue was partitioned between water and diethyl ether. The organic phase was separated and washed with water and brine before drying over anhydrous magnesium sulphate and evaporation in vacuo. The residue was purified by column chromatography on alumina eluting with 1:4 dichloromethane:hexane saturated with ammonia. 1-(Pent-4-ynyl)-4-propyl-2,6,7-trioxabicyclo[2.2.2]octane-3-carbonitrile was obtained as an oil (0.25 g). Gas-liquid chromatography (g.l.c): OV-17 at 175° produced one peak.

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