反応 #61074

反応方程式

NaBH4

cyanuric chloride

NMM

NH4Cl

5-(methyloxy)-2-nitrobenzoic acid

→

title compound

収率 53.0%

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

収率 53.0%

溶媒

water

Et2O

DME

DME

反応条件

後処理

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

実験手順

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%).

出典