Реакция #595321

ord-46d4d42143234c33aaa63af1caee4cdb

Уравнение реакции

O=S(=O)(Cl)C1CC1
Cyclopropanesulfonyl chloride
CCCCO
BuOH
c1ccncc1
pyridine
CCCCOS(=O)(=O)C1CC1
oil
Выход 71.0%
CCCCOS(=O)(=O)C1CC1
Butyl cyclopropanesulfonate
Выход 71.0%

Реагенты

Нет

Условия реакции

Температура
-10°CELSIUS
Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ТемператураThe mixture was slowly warmed at room temperature
  2. 2
    ДругоеThe solvent was removed under reduced pressure
  3. 3
    workup.DISSOLUTIONthe resulting white solid was dissolved in CHCl3
  4. 4
    ПромывкаThe organic phase was washed with water, brine
  5. 5
    Сушкаdried (MgSO4)
  6. 6
    Концентрированиеconcentrated

Методика

Cyclopropanesulfonyl chloride (5 g, 35 mmol, 1 eq) was dissolved in an excess BuOH (20 ml), the reaction mixture was cooled at −10° C. and pyridine (5.8 mL, 70 mmol, 2 eq) was slowly added dropwise. The mixture was slowly warmed at room temperature and stirred overnight. The solvent was removed under reduced pressure and the resulting white solid was dissolved in CHCl3. The organic phase was washed with water, brine and dried (MgSO4) and concentrated to give an oil (4.8 g, 24.9 mmol, 71%). 1H NMR (300 MHz, CDCl3): δ 4.25 (t, 2H), 2.46 (m, 1H), 1.74 (m, 2H), 1.45 (m, 2H), 1.25 (dd, 2H), 1.09 (dd, 2H), 0.93 (t, 3H).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US09095581B2uspto-grants-2015_08