Trifluoroacetic acid → HCID 19020973, compound

HRID 1109665Notes

Reaction equation

HRID 1109665 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][CH2:11][C:12]([C:31]([O:33][CH2:34][CH3:35])=[O:32])([C:26]([O:28][CH2:29][CH3:30])=[O:27])[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>[CH3:21][O:20][C:18]1[C:19]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][C:12]([C:31]([O:33][CH2:34][CH3:35])=[O:32])([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:13][C:14]=2[CH:15]=[C:16]([O:24][CH3:25])[C:17]=1[O:22][CH3:23]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19020968HCID 19020968, compound

Product 1

HCID 19020973HCID 19020973, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 3 ml of dichloromethane, 102 mg of diethyl 4-(3,4-methylenedioxyphenyl)-1-(3,4,5-trimethoxyphenyl)-butane-2,2-dicarboxylate [0.205 mmol, A. S. Kende and L. S. Liebeskind, J. Am. Chem. Soc., 98, 267 (1976)] were dissolved. The solution was added with 0.3 ml of trifluoroacetic acid and 210 mg (0.45 mmol) of ferric perchlorate, followed by stirring at room temperature for 1.5 hours. The reaction mixture was dissolved in 10 ml of ethyl acetate. After the resulting solution was washed with 2N-HCl and then 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: 1:3 mixed solvent of ethyl acetate and hexane), whereby 62 mg of the title compound were obtained as colorless oil (yield: 61%).

Workup

  1. dissolution, 98, 267 (1976)] were dissolved
  2. washAfter the resulting solution was washed with 2N-HCl
  3. dry with materialsaturated NaCl, the organic layer was dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure, whereby brown oil
  5. customwas obtained
  6. customThe oil thus obtained
  7. customwas purified by TLC (silica gel: "MERCK #5744", eluent: 1:3 mixed solvent of ethyl acetate and hexane)

Sources & evidence

ORD record
ord-f9b0d61ca8254732b1cec6693418c070
Source dataset
uspto-grants-1994_06
Patent number
US05321135

Reaction notes

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