Reacción #2069928

Ecuación de reacción

ethyl acetate

Cinnamoyl chloride

5-norbornene-2-methanol

triethylamine

→

5-norbornene 2-methylcinnamate

Rendimiento 88.0%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowere put into a 250 ml two-neck flask
2. 2
   Otroagitation was conducted in an ice-water bath at 0° C
3. 3
   workup.ADDITIONslowly added to the reactants
4. 4
   Otrowas conducted for an additional time of 1 hour
5. 5
   workup.ADDITIONThe solution was diluted
6. 6
   Otromoved to a separatory funnel
7. 7
   Lavadowashed with water and NaHCO3 a few times
8. 8
   workup.DISTILLATIONdistilled under reduced pressure
9. 9
   Otroto remove the solvent
10. 10
    OtroPurification
11. 11
    Otroto obtain a product

Procedimiento

After 5-norbornene-2-methanol (15 g, 0.121 mol), which was synthesized as described above, triethylamine (Aldrich, 61.2 g, 0.605 mol), and 20 ml of THF were put into a 250 ml two-neck flask, agitation was conducted in an ice-water bath at 0° C. Cinnamoyl chloride (22.1 g, 0.133 mol) was dissolved in 60 ml THF, and then slowly added to the reactants using an additional flask. After 10 min, the reactants were heated to room temperature, and agitation was conducted for an additional time of 1 hour. The solution was diluted using ethyl acetate, moved to a separatory funnel, washed with water and NaHCO3 a few times, and distilled under reduced pressure to remove the solvent. Purification was conducted using column chromatography (hexane:ethyl acetate=20:1) to obtain a product. (yield: 88%)

Fuente