Ammonium Chloride → 2-(4-Aminophenoxymethyl)-4,6-di-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran

HRID 367315Notes

Reaction equation

HRID 367315 reaction equation
C([O:4][C:5]1[C:6]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:7][C:8]2[O:12][C:11]([CH2:14][O:15][C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=3)([CH3:13])[CH2:10][C:9]=2[C:23]=1[C:24]([CH3:27])([CH3:26])[CH3:25])(=O)C.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[NH2:22][C:19]1[CH:18]=[CH:17][C:16]([O:15][CH2:14][C:11]2([CH3:13])[CH2:10][C:9]3[C:23]([C:24]([CH3:27])([CH3:26])[CH3:25])=[C:5]([OH:4])[C:6]([C:28]([CH3:29])([CH3:30])[CH3:31])=[CH:7][C:8]=3[O:12]2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 232880215-Acetoxy-2-(4-aminophenoxymethyl)-4,6-di-t-butyl-2-methyl-2,3-dihydrobenzofuran

Product 1

HCID 154857322-(4-Aminophenoxymethyl)-4,6-di-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuranYield 59%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under a nitrogen atmosphere, 1.2 g of 5-acetoxy-2-(4-aminophenoxymethyl)-4,6-di-t-butyl-2-methyl-2,3-dihydrobenzofuran was dissolved in 30 ml of toluene. To the solution was added 11.3 ml of diisobutyl aluminum hydride (1.0 M in toluene) and the mixture was stirred at room temperature 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 n-hexane containing 33% ethyl acetate to give 0.63 g of 2-(4-aminophenoxymethyl)-4,6-di-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran as a pale yellow oil (yield 59%).

Workup

  1. customAfter reaction
  2. filtrationinsoluble matters were filtered off on Celite
  3. extractionthe filtrate was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe concentrate was purified by silica gel column chromatography
  8. washeluting with n-hexane containing 33% ethyl acetate

Sources & evidence

ORD record
ord-0684820f75034b9697efc1f23b23868e
Source dataset
uspto-grants-2000_10
Patent number
US06133279

Reaction notes

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