Trifluoroacetic acid → HCID 10949004, compound

HRID 1109653Notes

Reaction equation

HRID 1109653 reaction equation
FC(F)(F)C(O)=O.[O:8]1[C:12]2[CH:13]=[CH:14][C:15](/[CH:17]=[C:18](\[CH2:23][C:24]3[CH:29]=[C:28]([O:30][CH3:31])[C:27]([O:32][CH3:33])=[C:26]([O:34][CH3:35])[CH:25]=3)/[C:19]([O:21][CH3:22])=[O:20])=[CH:16][C:11]=2[O:10][CH2:9]1>ClCCl.C(OCC)(=O)C>[CH3:35][O:34][C:26]1[C:25]2[C:14]3[C:15]([CH:17]=[C:18]([C:19]([O:21][CH3:22])=[O:20])[CH2:23][C:24]=2[CH:29]=[C:28]([O:30][CH3:31])[C:27]=1[O:32][CH3:33])=[CH:16][C:11]1[O:10][CH2:9][O:8][C:12]=1[CH:13]=3

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10960014HCID 10960014, compound

Product 1

HCID 10949004HCID 10949004, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ferric perchlorate hexahydrate (342 mg, 0.74 mmol) and 0.5 ml of trifluoroacetic acid were added to a solution of methyl (E)-α-(1,3-benzodioxol-5-yl-methylene)-3,4,5-trimethoxybenzene- propionate [114 mg, 0.295 mmol; P. Magnus et.al., J. Am. Chem. Soc., 107, 4984, (1985)] in 5 ml of dichloromethane, followed by stirring at room temperature for 1 hour. The reaction mixture was dissolved in 20 ml of ethyl acetate. The resulting solution was washed successively with 2N-HCl, water and saturated NaHCO3, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Brown oil thus obtained (122 mg) was purified by TLC (silica gel: "MERCK #5744", eluent: 1:1 mixed solvent of ethyl acetate and hexane), whereby 96 mg of the title compound were obtained as colorless oil (yield: 85%).

Workup

  1. washThe resulting solution was washed successively with 2N-HCl, water and saturated NaHCO3
  2. dry with materialby drying over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customBrown oil thus obtained (122 mg)
  5. customwas purified by TLC (silica gel: "MERCK #5744", eluent: 1:1 mixed solvent of ethyl acetate and hexane)

Sources & evidence

ORD record
ord-61b6264c04b144628536cf982c296f1a
Source dataset
uspto-grants-1994_06
Patent number
US05321135

Reaction notes

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