Methyl iodide → Butyl 1-methylcyclopropane-1-sulfonate

Temperature

-78 °C

To a solution of butyl cyclopropanesulfonate (1.5 g, 8.4 mmol, Preparation #6 Step A) in THF (8 mL) at about −78° C. was added n-BuLi (1.6 M in hexanes, 5.26 mL, 8.42 mmol) and iodomethane (0.684 mL, 10.9 mmol) simultaneously. 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 extracted with EtOAc (15 mL) and the combined organic extracts were dried over anhydrous MgSO4, filtered, and concd under reduced pressure. The residue was purified by silica gel column chromatography eluting with 5 to 25% EtOAc in heptanes 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 extracted with EtOAc (15 mL)
5. dry with materialthe combined organic extracts were dried over anhydrous MgSO4
6. filtrationfiltered
7. customThe residue was purified by silica gel column chromatography
8. washeluting with 5 to 25% EtOAc in heptanes

ORD record

ord-c0a53f5ead3f4737a1f5f199a2eca43b

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08426411B2