Reaction #2069928

Reaction equation

ethyl acetate

Cinnamoyl chloride

5-norbornene-2-methanol

triethylamine

→

5-norbornene 2-methylcinnamate

Yield 88.0%

Solvents

THF

THF

Conditions

Workup

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

Procedure

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%)

Source