Sesamol → HCID 19754900, compound

HRID 1588912Notes

Reaction equation

HRID 1588912 reaction equation
[CH:1]([N:4]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:5](=[O:13])[C:6]1[CH:11]=[CH:10][C:9](Br)=[CH:8][CH:7]=1)([CH3:3])[CH3:2].[CH2:20]1[O:28][C:27]2[CH:26]=[CH:25][C:24]([OH:29])=[CH:23][C:22]=2[O:21]1>N1C(C)=CC(C)=CC=1C.C(OCC)(=O)C>[CH:14]1([N:4]([CH:1]([CH3:3])[CH3:2])[C:5](=[O:13])[C:6]2[CH:11]=[CH:10][C:9]([O:29][C:24]3[CH:25]=[CH:26][C:27]4[O:28][CH2:20][O:21][C:22]=4[CH:23]=3)=[CH:8][CH:7]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 68289SesamolHCID 19754886HCID 19754886, compound

Product 1

HCID 19754900HCID 19754900, compound

Reagents, catalysts & solvents 2

HCID 79532,4,6-TrimethylpyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

The reaction was carried out in the same manner as described in Example 1 using p-bromobenzoic acid N-isopropyl-N-cyclohexyl amide (2.904 g, 8.96 mmol), 3,4-methylenedioxyphenol (1.354 g, 9.80 mmol) and cuprous oxide (641 mg, 4.48 mmol) in 2,4,6-collidine (15 ml). After 24 hr of refluxing, the reaction was cooled, diluted with ethyl acetate, and extracted with 0.5N HCl. A precipitate that formed on extraction was filtered and the aqueous filtrate was re-extracted with ethyl acetate. The organic layers were combined and washed three times with 6N HCl, twice with H2O, three times with 5% NaOH, twice with H2O and dried (Na2SO4) The drying agent was removed by filtration, and the filtrate concentrated in vacuo to give the crude product as a black oil. This was chromatographed on silica gel using mixtures of ethyl acetate and hexane as eluents to give the title compound as an oil.

Workup

  1. temperatureAfter 24 hr of refluxing
  2. temperaturethe reaction was cooled
  3. extractionextracted with 0.5N HCl
  4. customA precipitate that formed on extraction
  5. filtrationwas filtered
  6. extractionthe aqueous filtrate was re-extracted with ethyl acetate
  7. washwashed three times with 6N HCl
  8. dry with materialtwice with H2O, three times with 5% NaOH, twice with H2O and dried (Na2SO4) The drying agent
  9. customwas removed by filtration
  10. concentrationthe filtrate concentrated in vacuo
  11. customto give the crude product as a black oil
  12. customThis was chromatographed on silica gel using mixtures of ethyl acetate and hexane as eluents

Sources & evidence

ORD record
ord-6cdf5205e7dc4acf9251c45cbb8284de
Source dataset
uspto-grants-1993_06
Patent number
US05223539

Reaction notes

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