تفاعل #160575

معادلة التفاعل

1-butyl cyclopropanesulfonate

butyllithium

allyl iodide

→

titled product

المردود 69.0%

Butyl 1-allylcyclopropane-1-sulfonate

المردود 69.0%

المذيبات

THF

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المعالجة

1. 1
   أخرىThe volatiles were evaporated under reduced pressure
2. 2
   استخلاصthe residue extracted with CH2Cl2 (100 ml)
3. 3
   غسيلThe extract was washed with water
4. 4
   تجفيفdried (MgSO4)
5. 5
   أخرىevaporated
6. 6
   أخرىThe residue was purified over silica gel chromatography (eluants: hexane/CH2Cl2)

الإجراء التجريبي

To a solution of 1-butyl cyclopropanesulfonate (4.8 g, 24.9 mmol) in THF at −78° C. was added simultaneously butyllithium solution (15.6 ml, 24.9 mmol, 1.6M, THF) and allyl iodide (24.9 mmol) under nitrogen atmosphere. The reaction mixture was stirred 2 hours at −78° C. and 3 hours at room temperature. The volatiles were evaporated under reduced pressure and the residue extracted with CH2Cl2 (100 ml). The extract was washed with water, dried (MgSO4) and evaporated. The residue was purified over silica gel chromatography (eluants: hexane/CH2Cl2) to obtain the titled product (3.75 g, 69.0%) as a colorless oil, 1H NMR (300 MHz, CDCl3): δ 5.6 (m, 1H), 5.13-5.08 (t, 2H), 4.21 (t, 2H), 2.65 (d, 2H), 1.7 (m, 2H), 1.4 (m, 4H), 0.93 (m, 5H).

المصدر