Dichloromethane → HCID 19020981, compound

HRID 1109643Notes

Reaction equation

HRID 1109643 reaction equation
ClCCl.FC(F)(F)C(O)=O.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH2:23][CH:24]2[CH:29]([CH2:30][C:31]3[CH:36]=[C:35]([O:37][CH3:38])[C:34]([O:39][CH3:40])=[C:33]([O:41][CH3:42])[CH:32]=3)[CH2:28][O:27][C:25]2=[O:26])[CH:16]=[C:17]([O:21][CH3:22])[C:18]=1[O:19][CH3:20]>C(OCC)(=O)C>[CH3:42][O:41][C:33]1[C:34]([O:39][CH3:40])=[C:35]([O:37][CH3:38])[C:36]2[C:14]3[C:13]([O:12][CH3:11])=[C:18]([O:19][CH3:20])[C:17]([O:21][CH3:22])=[CH:16][C:15]=3[CH2:23][CH:24]3[C:25](=[O:26])[O:27][CH2:28][CH:29]3[CH2:30][C:31]=2[CH:32]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 99810052(3H)-Furanone, dihydro-3,4-bis[(3,4,5-trimethoxyphenyl)methyl]-

Product 1

HCID 19020981HCID 19020981, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Dissolved in a mixture consisting of 0.5 ml of dichloromethane and 0.05 ml of trifluoroacetic acid were 50 mg (0.112 mmol) of 2,3-bis[1-(3,4,5-trimethoxyphenyl)methyl]butanolide. The solution was added with 150 mg (0.32 mmol) of ferric perchlorate, followed by stirring at room temperature for 19 hours. The reaction mixture was dissolved in 10 ml of ethyl acetate. The resulting solution was washed successively with 2N-HCl, water and saturated NaHCO3. The organic layer was then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, whereby colorless oil was obtained. The oil was purified by thinlayer chromatography (TLC) (silica gel: "MERCK #5744", eluent: 1:3 mixed solvent of acetone and hexane), whereby 28.5 mg of the title compound were obtained as a colorless solid (yield: 57%).

Workup

  1. dissolutionDissolved in a mixture
  2. washThe resulting solution was washed successively with 2N-HCl, water and saturated NaHCO3
  3. dry with materialThe organic layer was then dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure, whereby colorless oil
  5. customwas obtained
  6. customThe oil was purified by thinlayer chromatography (TLC) (silica gel: "MERCK #5744", eluent: 1:3 mixed solvent of acetone and hexane)

Sources & evidence

ORD record
ord-a316d44c00d04860b3683075bcb36c7d
Source dataset
uspto-grants-1994_06
Patent number
US05321135

Reaction notes

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