反应详情

Lithium aluminum hydride (0.1116 g, 2.94 mmol, 1.5 eq) was added to a stirred solution of methyl 3-methoxy-5-nitrobenzoate (0.408 g, 1.96 mmol, 1 eq) in 10 ml anhydrous Et2O at 0° C. under Ar. The reaction was stirred at 0° C. to room temperature overnight. Starting material was still present after stirring overnight. Additional LAH (0.1116 g, 2.94 mmol, 1.5 eq) was added. After 2 h the reaction was quenched with water. The reaction was diluted with saturated aqueous NaHCO3 and extracted with EtOAc (×2). The combined organics were washed with brine (×1) and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo. Purification via flash chromatography yielded 0.2463 g (1.33 mmol, 68% yield) of (3-methoxy-5-nitrophenyl)methanol.

1. stirringafter stirring overnight
2. customAfter 2 h the reaction was quenched with water
3. additionThe reaction was diluted with saturated aqueous NaHCO3
4. extractionextracted with EtOAc (×2)
5. washThe combined organics were washed with brine (×1)
6. dry with materialdried over Na2SO4
7. filtrationThe inorganics were filtered off
8. customthe solvent was removed in vacuo
9. customPurification via flash chromatography