Реакция #2547

Уравнение реакции

sodium bicarbonate

3,4-dihydro-2H-pyrane

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

p-toluenesulfonic acid monohydrate

→

title compound

Выход 91.2%

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

Выход 91.2%

Растворители

methylene chloride

Условия реакции

Обработка

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

Методика

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.

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