반응 #2547

반응 방정식

sodium bicarbonate

3,4-dihydro-2H-pyrane

4-Hydroxymethyl-N-(2-methoxyphenyl)benzenesulfonamide

p-toluenesulfonic acid monohydrate

→

title compound

수율 91.2%

4-Tetrahydropyranyloxymethyl-N-(2-methoxyphenyl)benzenesulfonamide

수율 91.2%

용매

methylene chloride

반응 조건

후처리

1. 1
   온도with cooling in an ice bath
2. 2
   추출extracted with ether
3. 3
   세척The resulting organic layer was washed with saturated brine
4. 4
   건조dried on anhydrous magnesium sulfate
5. 5
   기타the solvent was removed by evaporation
6. 6
   기타Thereafter, the thus obtained light yellow oily material was purified by a silica gel column chromatography (ether:hexane=1:1)

실험 절차

4-Hydroxymethyl-N-(2-methoxyphenyl)benzenesulfonamide (99.6 mg, 0.34 mmol) was dissolved in methylene chloride (3 ml) to which, with cooling in an ice bath, were subsequently added 3,4-dihydro-2H-pyrane (48 μl, 0.51 mmol) and a catalytically effective amount of p-toluenesulfonic acid monohydrate. After 90 minutes of stirring at the same temperature, the reaction solution was mixed with saturated sodium bicarbonate aqueous solution (5 ml) and extracted with ether. The resulting organic layer was washed with saturated brine and dried on anhydrous magnesium sulfate, and the solvent was removed by evaporation. Thereafter, the thus obtained light yellow oily material was purified by a silica gel column chromatography (ether:hexane=1:1) to obtain 117 mg (91.2%) of the title compound in the form of colorless solid.

출처