3-Chloro-propane-1-sulfonic acid butyl ester → Butyl cyclopropanesulfonate

Temperature

0 °C

Solutions of 1-butyl 3-chloro-1-propanesulfonate (4.6 g, 21.39 mmol) in 25 ml THF) and of butyllithium (14.7 ml, 23.53 mmol, 1.6M, THF) were simultaneously added to THF (150 ml) at −78° C. under nitrogen atmosphere. The solution was allowed to warm to 0° C. and then quenched with water (2 ml). The volatiles evaporated under reduced pressure and the residue extracted with CH2Cl2 (150 ml). The extract was washed with water and dried (MgSO4) and evaporated to give crude desired product (3.23 g, 78.22%) in almost pure form as pale yellow oil which was used for next step without further purification. 1H NMR (300 MHz, CDCl3) δ 0.94 (t, J=7.5 Hz, 3H), 1.07 (m, 2H), 1.25 (m, 2H), 1.45 (sextet, 2H), 1.74 (quintet, 2H), 2.45 (heptet, 1H), 4.23 (t, J=6.6 Hz, 2H).

1. customquenched with water (2 ml)
2. customThe volatiles evaporated under reduced pressure
3. extractionthe residue extracted with CH2Cl2 (150 ml)
4. washThe extract was washed with water
5. dry with materialdried (MgSO4)
6. customevaporated

ORD record

ord-04fb435e702443ec8d5d1099e76732f7

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08829052B2