Chloride → 5-Norbornene 2-methylcinnamate

HRID 539388

Reaction equation

HRID 539388 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[CH2:8]O.C(N(CC)CC)C.[Cl-].[C:18]([O:21]CC)(=[O:20])[CH3:19]>C1COCC1>[CH:1]12[CH2:7][CH:4]([CH:3]=[CH:2]1)[CH2:5][CH2:6]2.[CH3:8][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH:7]=[CH:19][C:18]([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 312ChlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 78946Bicyclo(2.2.1)hept-5-ene-2-methanol

Product 1

HCID 866064575-Norbornene 2-methylcinnamateYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

15 g (0.121 mol) of the 5-norbornene-2-methanol prepared in Example 1, 61.2 g (0.605 mol) of triethylamine (produced from Aldrich Inc.), and 20 ml of THF were loaded into a 250 ml 2-neck flask and then stirred at 0° C. in an ice-water bath. 22.1 g (0.133 mol) of cinamoil chloride dissolved in 60 ml of THF was slowly added to the prepared mixture using an additional flask for 10 minutes. Then, the temperature of the reactant was increased to room temperature and then stirred for one hour. The resulting solution was diluted using an ethyl acetate. The diluted solution was loaded into a separatory funnel, washed using water and NaHCO3 several times, and then distilled in at a reduced pressure to remove a solvent. The result was refined using a column chromatography (Hexane: Ethyl acetate=20:1) to attain a product. (Yield: 88%)

Workup

  1. additionwas slowly added to the prepared mixture
  2. customfor 10 minutes
  3. temperatureThen, the temperature of the reactant was increased to room temperature
  4. stirringstirred for one hour
  5. additionThe resulting solution was diluted
  6. customThe diluted solution was loaded into a separatory funnel
  7. washwashed
  8. distillationdistilled in at a reduced pressure
  9. customto remove a solvent

Sources & evidence

ORD record
ord-b12ebf1f8c3b405fb78ffbe9a5a21978
Source dataset
uspto-grants-2014_10
Patent number
USRE045219E1

Linked notes

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