Methyl iodide → Benzyl 1-methylcyclopropane-1-sulfonate

Temperature

0 °C

n-BuLi (0.78 g, 12.25 mmol) was added drop-wise at −78° C. to a solution of Butylcyclopropane sulfonate (2.0 g, 11.2 mmol) in THF (20 mL) and continued stirring at the same temperature for 10 min. CH3I (3.98 g, 28.0 mmol) was added at −78° C., allowed the reaction to warm to 0° C. with stirring for 30 min. The reaction mixture was quenched with ice cold water, diluted with ethylacetate (100 mL), organic layer collected was dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the crude. The crude was purified by column chromatography (using silica gel and 4% ethyl acetate in Hexane as eluent) to afford benzyl 1-methylcyclopropane-1-sulfonate (Int-48) (2.0 g, 93% yield). 1H NMR (300 MHz, CD3OD) δ 4.2-4.1 (2H, t), 1.7-1.6 (2H, m), 1.4 (3H, s), 1.5-1.3 (2H, m), 1.3-1.2 (2H, m), 1.0-0.9 (2H, m), 0.9 (3H, t) ppm.

1. customthe reaction
2. stirringwith stirring for 30 min
3. customThe reaction mixture was quenched with ice cold water
4. additiondiluted with ethylacetate (100 mL), organic layer
5. customcollected
6. dry with materialwas dried over anhydrous sodium sulphate
7. concentrationconcentrated under reduced pressure
8. customto afford the crude
9. customThe crude was purified by column chromatography (using silica gel and 4% ethyl acetate in Hexane as eluent)

ORD record

ord-7f3b0c3eadb84975ace78d2bdbacaa7f

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394305B2