Trifluoroacetic acid → HCID 19020976, compound

HRID 1109664Notes

Reaction equation

HRID 1109664 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)=[CH:4][C:3]=2[O:2]1.FC(F)(F)C(O)=O>ClCCl.C(OCC)(=O)C>[CH3:25][O:24][C:16]1[C:15]2[C:6]3[CH:7]=[C:8]4[O:9][CH2:1][O:2][C:3]4=[CH:4][C:5]=3[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=2[CH:19]=[C:18]([O:20][CH3:21])[C:17]=1[O:22][CH3:23]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19020977HCID 19020977, compound

Product 1

HCID 19020976HCID 19020976, compoundYield 12.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 1 ml of dichloromethane, 73 mg (0.21 mmol) of 1-(3,4-methylenedioxyphenyl)-4-(3,4,5-trimethoxyphenyl)butane were dissolved. The solution was added with 0.1 ml of trifluoroacetic acid and 190 mg (0.41 mmol) of ferric perchlorate, followed by stirring at room temperature for 20 minutes. The reaction mixture was dissolved in 20 ml of ethyl acetate. After the resulting solution was washed with 2N-HCl and then with saturated NaCl, the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, whereby brown oil was obtained. The oil thus obtained was purified by TLC (silica gel: "MERCK #5744", eluent: 1:5 mixed solvent of ethyl acetate and hexane), whereby 9 mg of the title compound were obtained as colorless oil (yield: 12%). In addition, the starting material were recovered as colorless oil (13 mg, recovery: 18%).

Workup

  1. washAfter the resulting solution was washed with 2N-HCl
  2. dry with materialwith saturated NaCl, the organic layer was dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure, whereby brown oil
  4. customwas obtained
  5. customThe oil thus obtained
  6. customwas purified by TLC (silica gel: "MERCK #5744", eluent: 1:5 mixed solvent of ethyl acetate and hexane)

Sources & evidence

ORD record
ord-1af665fa50cd4880a075a7384f112316
Source dataset
uspto-grants-1994_06
Patent number
US05321135

Reaction notes

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