1-(Triphenylphosphoranylidene)acetone → HCID 54412413, compound

HRID 1087895Notes

Reaction equation

HRID 1087895 reaction equation
C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:8][C:9](=[O:11])[CH3:10])C=CC=CC=1.[F:24][CH2:25][CH2:26][O:27][C:28]1[C:35]([O:36][CH2:37][CH2:38][F:39])=[CH:34][CH:33]=[CH:32][C:29]=1[CH:30]=O>O1CCCC1>[CH3:8][C:9]([CH:10]=[CH:30][C:29]1[C:28]([O:27][CH2:26][CH2:25][F:24])=[C:35]([O:36][CH2:37][CH2:38][F:39])[CH:34]=[CH:33][CH:32]=1)=[O:11]

Participants

4

Reactant 2

HCID 150381-(Triphenylphosphoranylidene)acetoneHCID 15058684HCID 15058684, compound

Product 1

HCID 54412413HCID 54412413, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred, cold (0° C.) solution of 5.2 grams (0.016 mole) 1-triphenylphosphoranylidene-2-propanone in 50 ml of dry tetrahydrofuran was added dropwise a solution of 3.4 grams (0.015 mole) of 2,3-di(2-fluoroethoxy)benzaldehyde in 25 ml of dry tetrahydrofuran. After complete addition the reaction mixture was allowed to warm to room temperature and was then heated at reflux for three hours. The mixture was cooled to room temperature and stirred for approximately 18 hours. The solvent was removed by evaporation under reduced pressure leaving a residue. This residue was partitioned between diethyl ether and water. The organic phase was washed with an aqueous, saturated sodium chloride solution. The washed organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure leaving a brown residue. This residue was purified by column chromatography on silica gel, eluting with acetone:n-heptane (20:80), to yield 2.3 grams of 3-(methylcarbonylethenyl)-1,2-di(2-fluoroethoxy)benzene as a solid, mp 71°-72° C.

Workup

  1. additionAfter complete addition the reaction mixture
  2. temperaturewas then heated
  3. temperatureat reflux for three hours
  4. temperatureThe mixture was cooled to room temperature
  5. customThe solvent was removed by evaporation under reduced pressure
  6. customleaving a residue
  7. customThis residue was partitioned between diethyl ether and water
  8. washThe organic phase was washed with an aqueous, saturated sodium chloride solution
  9. dry with materialThe washed organic phase was dried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customThe filtrate was evaporated under reduced pressure
  12. customleaving a brown residue
  13. customThis residue was purified by column chromatography on silica gel
  14. washeluting with acetone:n-heptane (20:80)

Sources & evidence

ORD record
ord-f1efc527580a4ce58016812d04370b7a
Source dataset
uspto-grants-1990_10
Patent number
US04960884

Reaction notes

Loading…