Reaktion #61074

Reaktionsgleichung

NaBH4

cyanuric chloride

NMM

NH4Cl

5-(methyloxy)-2-nitrobenzoic acid

→

title compound

Ausbeute 53.0%

(5-Methoxy-2-nitro-phenyl)-methanol

Ausbeute 53.0%

Lösungsmittel

water

Et2O

DME

DME

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigea precipitate was formed
2. 2
   workup.STIRRINGthe reaction mixture was stirred for 4 hr
3. 3
   FiltrationThe suspension was filtered
4. 4
   workup.STIRRINGThe reaction mixture was stirred for 20 min at 0° C
5. 5
   SonstigeThe phases were separated
6. 6
   Extraktionthe aqueous layer was extracted with Et2O (2×100 mL)
7. 7
   WaschenThe combined organic extracts were washed with sat. aq. Na2CO3
8. 8
   Trocknendried over anh. Na2SO4
9. 9
   FiltrationThe solids were filtered
10. 10
    Sonstigethe solvent evaporated to dryness
11. 11
    SonstigeThe crude product was purified by flash chromatography (silica gel, cHex/EtOAc 8:2)

Vorschrift

To a suspension of cyanuric chloride (1.84 g, 1 eq) in anh. DME (60 mL) at r.t., under N2, was added NMM (1.1 mL, 1 eq). The reaction mixture was stirred for 2 min and a precipitate was formed. A solution of 5-(methyloxy)-2-nitrobenzoic acid (2.0 g, 10 mmol) in anh. DME (20 mL) was added and the reaction mixture was stirred for 4 hr. The suspension was filtered and a solution of NaBH4 (0.57 g, 1.5 eq) in water (30 mL) was added at 0° C. The reaction mixture was stirred for 20 min at 0° C. It was then diluted with Et2O (10 mL) and acidified to pH 5 by addition of sat. aq. NH4Cl. The phases were separated and the aqueous layer was extracted with Et2O (2×100 mL). The combined organic extracts were washed with sat. aq. Na2CO3 and dried over anh. Na2SO4. The solids were filtered and the solvent evaporated to dryness. The crude product was purified by flash chromatography (silica gel, cHex/EtOAc 8:2) to give the title compound (958 mg, 53%).

Quelle