HCID 23288043, compound → HCID 178475395, compound

HRID 367318Notes

Reaction equation

HRID 367318 reaction equation
[C:1]([O:4][C:5]1[C:6]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:7][C:8]2[O:12][C:11]([CH2:14][O:15][C:16]3[CH:21]=[CH:20][C:19]([CH:22]=O)=[CH:18][CH:17]=3)([CH3:13])[CH2:10][C:9]=2[C:24]=1[C:25]([CH3:28])([CH3:27])[CH3:26])(=[O:3])[CH3:2].[C:33]([NH:36][NH2:37])([NH2:35])=[NH:34].Cl>C(O)C.N1C=CC=CC=1>[C:1]([O:4][C:5]1[C:6]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:7][C:8]2[O:12][C:11]([CH2:14][O:15][C:16]3[CH:21]=[CH:20][C:19]([CH:22]=[N:37][NH:36][C:33]([NH2:35])=[NH:34])=[CH:18][CH:17]=3)([CH3:13])[CH2:10][C:9]=2[C:24]=1[C:25]([CH3:28])([CH3:27])[CH3:26])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 23288043HCID 23288043, compoundHCID 178418668HCID 178418668, compound

Product 1

HCID 178475395HCID 178475395, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

In a mixed solvent of 40 ml of ethanol and 16 ml of pyridine was dissolved 8.54 g of 5-acetoxy-4,6-di-t-butyl-2-(4-formylphenoxymethyl)-2-methyl-2,3-dihydrobenzofuran and 2.38 g of aminoguanidine hydrochloride was added at room temperature. After heating under reflux for 14 hours and then cooling, ethanol and excess pyridine were distilled off using an evaporator and the concentrate was combined with water and extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated. The concentrate was purified by silica gel column chromatography eluting with chloroform containing 5% methanol to give 9.31 g of 1-{4-[(5-acetoxy-4,6-di-t-butyl-2-methyl-2,3-dihydrobenzofuran-2-yl)methoxy]benzylideneamino}guanidine (rotamer mixture) as a pale yellow oil (yield 97%).

Workup

  1. additionwas added at room temperature
  2. temperatureAfter heating
  3. temperatureunder reflux for 14 hours
  4. temperaturecooling
  5. distillationethanol and excess pyridine were distilled off
  6. customan evaporator
  7. extractionextracted with ethyl acetate
  8. washthe organic layer was washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated
  11. customThe concentrate was purified by silica gel column chromatography
  12. washeluting with chloroform containing 5% methanol

Sources & evidence

ORD record
ord-196b901de1424c8cb562c75707133c7c
Source dataset
uspto-grants-2000_10
Patent number
US06133279

Reaction notes

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