تفاعل #595321

ord-46d4d42143234c33aaa63af1caee4cdb

معادلة التفاعل

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

الكواشف

لا شيء

ظروف التفاعل

درجة الحرارة
-10°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةThe mixture was slowly warmed at room temperature
  2. 2
    أخرىThe solvent was removed under reduced pressure
  3. 3
    workup.DISSOLUTIONthe resulting white solid was dissolved in CHCl3
  4. 4
    غسيلThe organic phase was washed with water, brine
  5. 5
    تجفيفdried (MgSO4)
  6. 6
    تركيزconcentrated

الإجراء التجريبي

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).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09095581B2uspto-grants-2015_08