Реакция #57802

Уравнение реакции

4-methyl-4-phenyl-tetrahydro-pyran

chlorosulfonic acid

→

4-(4-Methyl-tetrahydro-pyran-4-yl)-benzenesulfonyl Chloride

Растворители

methylene chloride

Условия реакции

Обработка

1. 1
   Температураcooled in an ice bath
2. 2
   workup.ADDITIONthe reaction was added to ice
3. 3
   Экстракцияthe product was extracted with methylene chloride (3×100 mL)
4. 4
   ПромывкаThe organic layer was washed with saturated brine
5. 5
   Сушкаdried (MgSO4)
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated
8. 8
   Другоеe product was chromatographed on silica gel
9. 9
   ДругоеRemoval of solvent
10. 10
    Другоеprovided pure product as a colorless syrup which
11. 11
    Другоеcrystallized

Методика

To a magnetically stirred mixture of 4-methyl-4-phenyl-tetrahydro-pyran (1.10 g, 6.24 mmol) in dry methylene chloride (50 mL) cooled in an ice bath was added 2.07 mL of chlorosulfonic acid (3.64 g, 31.2 mmol) dropwise under dry nitrogen. The reaction was stirred overnight at room temperature; the reaction was added to ice and the product was extracted with methylene chloride (3×100 mL). The organic layer was washed with saturated brine, dried (MgSO4), filtered and concentrated. e product was chromatographed on silica gel using ethyl acetate-hexane mixtures (2-20% hexane). Removal of solvent provided pure product as a colorless syrup which crystallized on standing: 1H NMR (CDCl3) δ 7.99 (d, 2H, J=8.8 Hz), 7.56 (d, 2H, J=8.8 Hz), 3.79 (ddd, 1H, J=11.7 Hz, J=8.4 Hz, J=3.3 Hz), 3.70 (ddd, 1H, J=11.7 Hz, J=6.0 Hz, J=3.8 Hz), 2.11 (ddd, 1H, J=13.8 Hz, J=8.4 Hz, J=3.8 Hz), 1.81 (dm, 1H, J=13.8 Hz), 1.35 (s, 3H). MS: m/z 275 (M++1).

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