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-d91d8ed404e84d39b56aac3d09d5d6d1

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08829052B2