반응 #1563940

반응 방정식

n-BuLi

Benzylcyclopropane sulfonate

CH3I

→

benzyl 1-methylcyclopropane-1-sulfonate

용매

THF

반응 조건

후처리

1. 1
   기타the reaction
2. 2
   workup.STIRRINGwith stirring for 30 min
3. 3
   기타The reaction mixture was quenched with ice cold water
4. 4
   workup.ADDITIONdiluted with ethylacetate (100 mL), organic layer
5. 5
   기타collected
6. 6
   건조was dried over anhydrous sodium sulphate
7. 7
   농축concentrated under reduced pressure
8. 8
   기타to afford the crude
9. 9
   기타The crude was purified by column chromatography (using silica gel and 4% ethyl acetate in Hexane as eluent)

실험 절차

n-BuLi (0.78 g, 12.25 mmol) was added drop-wise at −78° C. to a solution of Benzylcyclopropane 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-25). 1H NMR (300 MHz, CD3OD) δ ppm 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).

출처