Reaktion #309125

Reaktionsgleichung

2-bromo-naphthalene-1,4-dicarboxylic acid diisopropyl ester

diisobutylaluminum hydride

toluene

ammonium chloride

→

titled compound

Ausbeute 91.9%

(2-bromo-4-hydroxymethyl-naphthalene-1-yl)-methanol

Ausbeute 91.9%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction
2. 2
   ExtraktionThe resultant mixture was twice extracted with ethyl acetate
3. 3
   TrocknenAfter drying the organic layer over anhydrous magnesium sulfate, solvent
4. 4
   Sonstigewas removed by distillation under reduced pressure
5. 5
   SonstigeThe resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:1))

Vorschrift

Under a nitrogen stream, to a solution of 2-bromo-naphthalene-1,4-dicarboxylic acid diisopropyl ester (191.5 mg, 0.505 mmol) in dichloromethane (1.9 mL) was added a solution of diisobutylaluminum hydride in toluene (1.04 M, 4.9 mL, 5.096 mmol) at −78° C. The temperature of the resultant mixture was raised over 2 hours to 0° C., and then to the solution was added saturated aqueous ammonium chloride to stop the reaction. The resultant mixture was twice extracted with ethyl acetate. After drying the organic layer over anhydrous magnesium sulfate, solvent was removed by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:1)), to thereby obtain the titled compound (124 mg, 87%).

Quelle