반응 #216445

반응 방정식

Boron trifluoride etherate

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

Triethylamine

→

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

용매

dichloromethane

반응 조건

후처리

1. 1
   기타the solvent was removed in vacuo
2. 2
   기타The residue was partitioned between diethyl ether and water
3. 3
   기타The organic phase was separated
4. 4
   세척further washed with water and brine
5. 5
   건조before drying over anhydrous magnesium sulphate
6. 6
   기타The solvent was evaporated in vacuo
7. 7
   기타the residue was purified by column chromatography on alumina eluting with 1:6 dichloromethane

실험 절차

Boron trifluoride etherate (0.18 ml) was added to a stirred solution of (3-propyloxetan-3-yl)methyl hex-5-ynoate (1.33 g.) in dry dichloromethane (25 ml) at -70°. The mixture was allowed to warm to room temperature over 16 hours. Triethylamine (0.28 ml) was then added and the solvent was removed in vacuo. The residue was partitioned between diethyl ether and water. The organic phase was separated and further washed with water and brine before drying over anhydrous magnesium sulphate. The solvent was evaporated in vacuo and the residue was purified by column chromatography on alumina eluting with 1:6 dichloromethane:hexane saturated with ammonia. 1-(Pent-4-ynyl)-4-propyl-2,6,7-trioxabicyclo[2.2.2]octane was obtained as a colourless oil which crystallised on trituration (0.64 g) with hexane.

출처