Reacción #1350131

Ecuación de reacción

3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraen-1-ol

p-toluenesulfonic acid

2,3-dihydropyran

→

1-(2-tetrahydropyranyl)oxy-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraene

Rendimiento 68.0%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONto the solution was dropwise added
2. 2
   workup.STIRRINGThe resulting solution was further stirred at 0°-5° C. for 30 min.
3. 3
   Lavadowashed with an aqueous sodium carbonate solution in a separatory funnel
4. 4
   ConcentraciónThe solution was concentrated after the washing
5. 5
   Otrothe concentrated solution was purified over a silica gel column

Procedimiento

In methylene chloride were dissolved 15 g of 3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraen-1-ol and 1.5 g of p-toluenesulfonic acid, and to the solution was dropwise added, under stirring, 8.7 g of 2,3-dihydropyran, at 0°-5° C. and over a period of 30 min. The resulting solution was further stirred at 0°-5° C. for 30 min., and then washed with an aqueous sodium carbonate solution in a separatory funnel. The solution was concentrated after the washing, and the concentrated solution was purified over a silica gel column to give 13 g of 1-(2-tetrahydropyranyl)oxy-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraene (yield 68%).

Fuente