Ammonium Chloride → HCID 178431211, compound

HRID 367316Notes

Reaction equation

HRID 367316 reaction equation
C([O:4][C:5]1[C:6]([C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:7][C:8]2[O:12][C:11]([CH2:14][O:15][C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH2:25])=[NH:24])=[CH:18][CH:17]=3)([CH3:13])[CH2:10][C:9]=2[C:26]=1[C:27]([CH3:30])([CH3:29])[CH3:28])(=O)C.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[C:27]([C:26]1[C:9]2[CH2:10][C:11]([CH2:14][O:15][C:16]3[CH:17]=[CH:18][C:19]([NH:22][C:23]([NH2:25])=[NH:24])=[CH:20][CH:21]=3)([CH3:13])[O:12][C:8]=2[CH:7]=[C:6]([C:31]([CH3:34])([CH3:33])[CH3:32])[C:5]=1[OH:4])([CH3:30])([CH3:28])[CH3:29]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21225700Diisobutylaluminumhydride2×HCID 178475396HCID 178475396, compound

Product 1

HCID 178431211HCID 178431211, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under a nitrogen atmosphere, 1.4 g of 1-{4-[(5-acetoxy-4,6-di-t-butyl-2-methyl-2,3-dihydrobenzofuran-2-yl)methoxy]phenyl}guanidine was dissolved in 50 ml of toluene. To the solution was added 12 ml of diisobutyl aluminum hydride (1.0 M in toluene) and the mixture was stirred at room temperature for 14 hours. After further addition of 6 ml of diisobutyl aluminum hydride (1.0 M in toluene) at room temperature, the mixture was heated under reflux for 2 hours. After reaction, a saturated aqueous ammonium chloride solution was added, and insoluble matters were filtered off on Celite and the filtrate was extracted with ethyl acetate. 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 10% methanol to give 0.67 g of 1-{4-[(4,6-di-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran-2-yl)methoxy]phenyl}guanidine as a pale yellow oil (yield 52%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customAfter reaction
  4. filtrationinsoluble matters were filtered off on Celite
  5. extractionthe filtrate was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe concentrate was purified by silica gel column chromatography
  10. washeluting with chloroform containing 10% methanol

Sources & evidence

ORD record
ord-d4ec278fb8ff49808e5af3d98e56acb8
Source dataset
uspto-grants-2000_10
Patent number
US06133279

Reaction notes

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