反应详情

温度

75 °C

To a stirring solution of 234 mg of 3-(methoxycarbonyl)-5-(N-methylmethylsulfonamido)benzoic acid in 10 mL of THF at r.t. was added 1.2 mL of BH3.THF (1.0 M in THF). After the solution was stirred at 75° C. for 3 h, 3 mL of acetic acid:H2O (1:1) was added and stirring was continued until bubbling ceased. Saturated NaHCO3 solution was added to a pH=7, and the solution was concentrated. Water was added, and the aqueous layer was extracted with EtOAc (2×). The combined extracts were washed with water and brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (1.5% MeOH/CHCl3) provided 191 mg of methyl 3-(hydroxymethyl)-5-(N-methylmethylsulfonamido)benzoate as a pale yellow oil in 86% yield.

1. stirringstirring
2. customuntil bubbling
3. additionSaturated NaHCO3 solution was added to a pH=7
4. concentrationthe solution was concentrated
5. additionWater was added
6. extractionthe aqueous layer was extracted with EtOAc (2×)
7. washThe combined extracts were washed with water and brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated
11. customPurification by flash silica gel chromatography (1.5% MeOH/CHCl3)