HCID 19020966, compound → HCID 19020977, compound

HRID 1109661Notes

Reaction equation

HRID 1109661 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10](O)[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>C(OCC)(=O)C.[Pd](Cl)Cl>[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:15]=[C:16]([O:24][CH3:25])[C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=3)=[CH:4][C:3]=2[O:2]1

Participants

4

Reactant 1

HCID 19020966HCID 19020966, compound

Product 1

HCID 19020977HCID 19020977, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Dissolved in 20 ml of ethyl acetate were 500 mg (1.39 mmol) of 1-(3,4-methylenedioxyphenyl)-4-(3,4,5-trimethoxyphenyl)butan-1-ol, followed by the addition of 5 mg of palladium chloride. The resulting mixture was stirred at room temperature for 15 hours under a hydrogen atmosphere of 1 atm. Insoluble matter was removed by filtration and the filtrate was then concentrated. The concentrate thus obtained was purified by column chromatography (silica gel: "MERCK #9385", 50 g, eluent: 1:5 mixed solvent of ethyl acetate and hexane), whereby 388 mg of the title compound were obtained as colorless oil (yield: 81%).

Workup

  1. customInsoluble matter was removed by filtration
  2. concentrationthe filtrate was then concentrated
  3. concentrationThe concentrate thus
  4. customobtained
  5. customwas purified by column chromatography (silica gel: "MERCK #9385", 50 g, eluent: 1:5 mixed solvent of ethyl acetate and hexane)

Sources & evidence

ORD record
ord-b9ce352800b94a319a922baaca316b77
Source dataset
uspto-grants-1994_06
Patent number
US05321135

Reaction notes

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