反応 #160575

反応方程式

1-butyl cyclopropanesulfonate

butyllithium

allyl iodide

→

titled product

収率 69.0%

Butyl 1-allylcyclopropane-1-sulfonate

収率 69.0%

溶媒

THF

反応条件

後処理

1. 1
   その他The volatiles were evaporated under reduced pressure
2. 2
   抽出the residue extracted with CH2Cl2 (100 ml)
3. 3
   洗浄The extract was washed with water
4. 4
   乾燥dried (MgSO4)
5. 5
   その他evaporated
6. 6
   その他The residue was purified over silica gel chromatography (eluants: hexane/CH2Cl2)

実験手順

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).

出典