Methyl iodide → Butyl 1-methylcyclopropane-1-sulfonate

Temperature

0 °C

To a solution of 1-Butyl cyclopropanesulfonate (1 g, 5.58 mmol) in THF (15 ml) butyllithium solution (3.84 ml, 6.14 mmol, 1.6M, THF) was slowly added at −78° C. under nitrogen atmosphere. After 15 minutes MeI (0.72 ml, 11.16 mmol) was added and the solution was allowed to warm to 0° C. and quenched with water (1 ml). The volatiles 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 (0.59 g, 55.0%) as a colorless oil. 1H NMR (300 MHz, CDCl3)) δ 0.84 (m, 2H), 0.95 (t, J=7.2 Hz, 3H), 1.43 (m, 4H), 1.53 (s, 3H), 1.74 (m, 2H), 4.21 ((t, J=6.6 Hz, 2H).

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

ORD record

ord-f71a18ab2e494356b7eac726836c6512

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08648116B2