Hydrochloric Acid → HCID 18768837, compound

HRID 480095Notes

Reaction equation

HRID 480095 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[CH:8][C:7]=1[C:15]([O:17][CH3:18])=[O:16].C[O-].[Na+].[F:22][C:23]([F:30])([F:29])[C:24](OCC)=[O:25].Cl>CC(OC)(C)C.CO.C(OCC)(=O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH2:13][C:24](=[O:25])[C:23]([F:30])([F:29])[F:22])=[CH:8][C:7]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 9794Ethyl trifluoroacetateHCID 10942334Sodium Methoxide2×HCID 18768827HCID 18768827, compound

Product 1

HCID 18768837HCID 18768837, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

4-(2-furyl)-3-(methoxycarbonyl)phenyl-1-ethanone (1.36 g, 5.57 mmol) was dissolved in MTBE (30 ml) at room temperature under nitrogen. Ethyl trifluroroacetate (0.87 g, 6.1 mmol) was added followed by a suspension of sodium methoxide (0.36 g, 6.7 mmol) in methanol (5 ml). After 2 hours of stirring, ethyl trifluoroacetate (2.03 g, 14.3 mmol) was added, followed by sodium methoxide (0.87 g, 6.1mmol). After an additional 18 hours, the mixture was poured into stirring ethyl acetate and dilute hydrochloric acid. The organic layer was washed with water and brine, dried over sodium sulfate, filtered, and evaporated to give the title compound.

Workup

  1. additionEthyl trifluroroacetate (0.87 g, 6.1 mmol) was added
  2. waitAfter an additional 18 hours
  3. additionthe mixture was poured
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-711604da4e9143dbb98878e34b07ed03
Source dataset
uspto-grants-2003_11
Patent number
US06649636B1

Reaction notes

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