Pyridine → HCID 21960507, compound

HRID 2211564Notes

Reaction equation

HRID 2211564 reaction equation
N1C=C[CH:4]=[CH:3][CH:2]=1.[C:7]1([C:13]2[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[O:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>>[C:13]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:21]=[CH:20][C:16]([C:17]([O:22][CH:26]2[CH2:2][CH:3]3[CH2:4][CH:25]2[CH:24]=[CH:23]3)=[O:18])=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 841514-Phenylbenzoyl chloride

Product 1

HCID 21960507HCID 21960507, compound

Conditions

Temperature
4 °C

Procedure

28 g (253.9 m mol) of norbornene alcohol (with an endo form/exo form molar ratio of 8/1) was measured into a 500 mL flask equipped with a dropping funnel, and the air inside the system was replaced with nitrogen. 41 mL (507.8 m mol) of pyridine was then added dropwise and stirred well until dissolved. Subsequently, with the temperature of the reaction system maintained at 4±2° C. by cooling in an ice bath, a solution of 50 g (230.8 m mol) of 4-phenylbenzoyl chloride dissolved in 200 mL of dry THF (tetrahydrofuran) was gradually dropped into the reaction solution with constant stirring, and following completion of the addition, stirring was continued for 1 hour with the reaction vessel still in the ice bath, and then for 1 hour at room temperature, and then for a further 30 minutes under reflux. Following cooling of the reaction mixture to room temperature, the generated pyridine salt was removed by filtration through filter paper, and the reaction mixture was well washed with distilled water. The solvent was then removed by heating under reduced pressure, and the product crystals were repeatedly recrystallized from n-hexane to yield 63 g of white crystals of 5-(4-biphenylcarbonyloxy)bicyclo[2.2.1]hept-2-ene (monomer). Analysis of the product crystals by HPLC revealed a purity of 98%.

Workup

  1. customequipped with a dropping funnel
  2. dissolutionuntil dissolved
  3. temperatureby cooling in an ice bath
  4. additionwas gradually dropped into the reaction solution with constant stirring
  5. additioncompletion of the addition
  6. stirringstirring
  7. temperaturefor a further 30 minutes under reflux
  8. temperatureFollowing cooling of the reaction mixture to room temperature
  9. customthe generated pyridine salt was removed by filtration
  10. filtrationthrough filter paper
  11. washthe reaction mixture was well washed with distilled water
  12. customThe solvent was then removed
  13. temperatureby heating under reduced pressure
  14. customthe product crystals were repeatedly recrystallized from n-hexane

Sources & evidence

ORD record
ord-dc9dd5d76adc48fe9d865ecb73c258af
Source dataset
uspto-grants-2006_09
Patent number
US07101498B2

Reaction notes

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