Reaktion #454493

Reaktionsgleichung

1-amino-3-[(5-acetoxy-4,6-di-t-butyl-2-methyl-2,3-dihydrobenzofuran-2-yl)methyl]guanidine

diisobutyl aluminum hydride

ammonium chloride

→

1-amino-3-[(4,6-di-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran-2-yl)methyl]guanidine

Ausbeute 37.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter reaction
2. 2
   Filtrationinsoluble matters were filtered off on Celite
3. 3
   ExtraktionThe filtrate was extracted with ethyl acetate
4. 4
   Waschenthe organic layer was washed with saturated brine
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe concentrate was purified by silica gel column chromatography
8. 8
   Wascheneluting with chloroform containing 10% methanol

Vorschrift

Under a nitrogen atmosphere, 0.98 g of 1-amino-3-[(5-acetoxy-4,6-di-t-butyl-2-methyl-2,3-dihydrobenzofuran-2-yl)methyl]guanidine was dissolved in 50 ml of toluene. To the solution was added 10 ml of diisobutyl aluminum hydride (1.0 M in toluene) and the mixture was stirred at room temperature for 1 hour. After reaction, a saturated aqueous ammonium chloride solution was added and insoluble matters were filtered off on Celite. The filtrate was 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 10% methanol to give 0.32 g of 1-amino-3-[(4,6-di-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran-2-yl)methyl]guanidine as a white crystal (yield 37%).

Quelle