Allyl iodide → Butyl 1-allylcyclopropane-1-sulfonate

Temperature

-78 °C

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).

1. customThe volatiles were evaporated under reduced pressure
2. extractionthe residue extracted with CH2Cl2 (100 ml)
3. washThe extract was washed with water
4. dry with materialdried (MgSO4)
5. customevaporated
6. customThe residue was purified over silica gel chromatography (eluants: hexane/CH2Cl2)

ORD record

ord-6417b1cd76bc42e48b364fbb7fefbe73

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08101799B2