Methyl iodide → Butyl 1-methylcyclopropane-1-sulfonate

Temperature

-78 °C

To a solution of butyl cyclopropanesulfonate (1.5 g, 8.4 mmol) in THF (8 mL) at about −78° C., n-BuLi (1.6 M in hexanes, 5.26 mL, 8.42 mmol) and iodomethane (0.684 mL, 10.9 mmol) were added simultaneously and the resulting mixture was stirred at about −78° C. for about 2 h and then at ambient temperature for about 2 h. The reaction was quenched by the addition of saturated aqueous NH4Cl (7 mL) and the layers were separated. The aqueous layer was back extracted with EtOAc (15 mL) and the combined organic extracts were dried over anhydrous MgSO4 and concd under reduced pressure. The residue was subjected to silica gel column chromatography (5 to 25% EtOAc in heptane over 30 min) to yield butyl 1-methylcyclopropane-1-sulfonate (0.8 g, 49%) as a colorless oil. 1H NMR (DMSO-d6) δ 4.17 (t, 2H), 1.62 (m, 2H), 1.43 (s, 3H), 1.35 (m, 2H), 1.22 (m, 2H), 0.94 (m, 2H), 0.88 (t, 3H).

1. waitat ambient temperature for about 2 h
2. customThe reaction was quenched by the addition of saturated aqueous NH4Cl (7 mL)
3. customthe layers were separated
4. extractionThe aqueous layer was back extracted with EtOAc (15 mL)
5. dry with materialthe combined organic extracts were dried over anhydrous MgSO4 and concd under reduced pressure
6. customwas subjected to silica gel column chromatography (5 to 25% EtOAc in heptane over 30 min)

ORD record

ord-2332e7158e464f34932409781308050b

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08426411B2