Potassium Hydroxide → 3-(4-Fluorobenzylidene)bicyclo[2.2.2]oct-5-en-2-one

HRID 1200178Notes

Reaction equation

HRID 1200178 reaction equation
[CH:1]12[CH2:8][CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][C:2]2=[O:9].[F:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1.[OH-].[K+]>CC(O)C.O.CCOCC>[F:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[C:3]2[CH:4]3[CH2:7][CH2:8][CH:1]([CH:6]=[CH:5]3)[C:2]2=[O:9])=[CH:13][CH:12]=1

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 680234-FluorobenzaldehydeHCID 137507Bicyclo[2.2.2]oct-5-en-2-one

Product 1

HCID 572081603-(4-Fluorobenzylidene)bicyclo[2.2.2]oct-5-en-2-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

A solution of bicyclo[2.2.2]oct-5-en-2-one (J. Oro. Chem. 33, 2211 (1968)) (3.34 g, 27.4 mmoles), 4-fluorobenzaldehyde (3.08 ml, 28.7 mmoles) and KOH (2 pellets) in 10 ml of 2-propanol was heated at 60° C. for 1.5 hours, cooled to room temperature and diluted with H2O and ether. The organic layer was washed with H2O, 2% aqueous HCl, saturated NaHCO3 and brine and dried (MgSO4). Removal of the volatiles in vacuo provided a residue which was recrystallized with hexanes. mp 85°-86° C.

Workup

  1. washThe organic layer was washed with H2O, 2% aqueous HCl, saturated NaHCO3 and brine
  2. dry with materialdried (MgSO4)
  3. customRemoval of the volatiles in vacuo
  4. customprovided a residue which
  5. customwas recrystallized with hexanes

Sources & evidence

ORD record
ord-ef48610c1da141679b4906a0416b8fe9
Source dataset
uspto-grants-1990_02
Patent number
US04904692

Reaction notes

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