Hydrochloric Acid → HCID 14677866, compound

HRID 1199434Notes

Reaction equation

HRID 1199434 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=O)=[CH:4][CH:3]=1.[O:15]=[C:16]([CH:18]=[C:19]([CH3:21])[CH3:20])[CH3:17].B(F)(F)F.CCOCC.Cl>CCOCC.C([O-])(O)=O.[Na+].CO>[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]2[CH:8]([C:9]([O:11][CH3:12])=[O:10])[C:19]([CH3:21])([CH3:20])[CH2:18][C:16](=[O:15])[CH:17]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8000Boron trifluoride etherateHCID 8858Mesityl oxideHCID 579425Methyl 4-fluorobenzoylacetate

Product 1

HCID 14677866HCID 14677866, compoundYield 37,190.602%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of methyl 4-fluorobenzoylacetate (20.03 g, 97 mmoles), mesityl oxide (14.58 g, 0.145 mmoles) and borontrifluoride etherate (13.77 g, 97 mmoles) was kept at 0° C. for 3 days and diluted with ether and saturated NaHCO3. The organic layer was washed with brine and dried (MgSO4). Removal of the volatiles in vacuo provided a residue which was diluted with 200 ml anhydrous methanol and 20 ml of Triton-B. The mixture was heated at reflux 2 hours, cooled, acidified with aqueous HCl and extracted with ether. The organic layers were washed with aqueous HCl, water and brine and dried (MgSO4). Removal of the volatiles in vacuo provided a residue which was purified by HPLC using 8% ethyl acetate in hexanes as the eluent. Concentration in vacuo of the product-rich fractions provided 14.9 g of the oily product.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried (MgSO4)
  3. customRemoval of the volatiles in vacuo
  4. customprovided a residue which
  5. temperatureThe mixture was heated
  6. temperatureat reflux 2 hours
  7. temperaturecooled
  8. extractionextracted with ether
  9. washThe organic layers were washed with aqueous HCl, water and brine
  10. dry with materialdried (MgSO4)
  11. customRemoval of the volatiles in vacuo
  12. customprovided a residue which
  13. customwas purified by HPLC
  14. concentrationConcentration in vacuo of the product-rich fractions

Sources & evidence

ORD record
ord-dbd8cc2ab06b4e53ae0796133b9018a6
Source dataset
uspto-grants-1990_02
Patent number
US04900754

Reaction notes

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