Hydrochloric Acid → HCID 86744985, compound

HRID 2248300Notes

Reaction equation

HRID 2248300 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:13](OC)(=[O:17])[C:14]([CH3:16])=[CH2:15].CC(C)([O-])C.[K+].Cl>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[C:13](=[O:17])[C@@H:14]([CH3:16])[CH2:15][C@@H:8]2[C:9]([O:11][CH3:12])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6658Methyl MethacrylateHCID 2734108Methyl 3-fluorophenylacetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 86744985HCID 86744985, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 3-fluorophenylacetate (prepared from 3 fluorophenylacetic acid (Aldrich Chem. Co., Madison, Wis.) via esterification with methanol catalyzed by gaseous HCl) in anhydrous N,N-dimethylformamide (40 mL) warmed to 70° C. was added methyl methacrylate (5.8 mL) and potassium tertbutoxide (0.55 gm). After 15 minutes, aqueous 1N HCl (75 mL) was added, and the mixture extracted with diethyl ether. The organic extracts were washed with H2O, brine, dried (Na2SO4, filtered and evaporated. The residue was dissolved in concentrated H2SO4 (80 mL)/H2O (20 mL), and warmed to 70° C. for 3 hours, then poured onto crushed ice, and the mixture extracted with ethyl acetate. The extracts were washed with H2O, brine, dried (Na2SO4, filtered and evaporated. The oily residue was dissolved in methanol (250 mL), and the solution saturated with gaseous HCl. After 30 minutes, the mixture was purged with nitrogen, and concentrated under reduced pressure. The oily residue was partitioned between H2O (500 mL), and ethyl acetate, and the organic layer washed with water, brine, dried (Na2SO4), filtered and concentrated in vacuo to yield the title compound (10.9 gm, Rf (1:1 diethyl ether/SiO2)=0.4).

Workup

  1. extractionthe mixture extracted with diethyl ether
  2. washThe organic extracts were washed with H2O, brine
  3. dry with materialdried (Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionThe residue was dissolved in concentrated H2SO4 (80 mL)/H2O (20 mL)
  7. additionpoured
  8. customonto crushed ice
  9. extractionthe mixture extracted with ethyl acetate
  10. washThe extracts were washed with H2O, brine
  11. dry with materialdried (Na2SO4
  12. filtrationfiltered
  13. customevaporated
  14. dissolutionThe oily residue was dissolved in methanol (250 mL)
  15. waitAfter 30 minutes
  16. customthe mixture was purged with nitrogen
  17. concentrationconcentrated under reduced pressure
  18. customThe oily residue was partitioned between H2O (500 mL), and ethyl acetate
  19. washthe organic layer washed with water, brine
  20. dry with materialdried (Na2SO4)
  21. filtrationfiltered
  22. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-97fe78f45cb04eda986b4731987ba730
Source dataset
uspto-grants-1991_08
Patent number
US05039672

Reaction notes

Loading…