3-(iodomethyl)-1,1-dimethoxycyclobutane

3-(iodomethyl)-1,1-dimethoxycyclobutane Property

storage temp. 

2-8°C(protect from light)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3-(iodomethyl)-1,1-dimethoxycyclobutane Chemical Properties,Usage,Production

Synthesis

A solution of triphenylphosphine (2.42 g, 9.25 mmol) and imidazole (1.26 g, 18.49 mmol) in dichloromethane (20 mL) was added to a round-bottomed flask and cooled to 0°C in an ice bath. To this cooled solution was added iodine (2.35 g, 9.25 mmol). After the iodine was completely dissolved, a solution of (3,3-dimethoxycyclobutyl) methanol (1.04 g, 7.11 mmol) in dichloromethane (10 mL) was added. The reaction mixture was stirred at 0°C for 30 minutes, followed by continued stirring at 25°C for 2 hours. Upon completion of the reaction, the reaction was poured into ice-cold water (50 mL) and extracted with dichloromethane (2 × 30 mL). The organic layers were combined, washed with 1.0 N sodium thiosulfate solution (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by fast column chromatography (Merck silica gel 60, 230-400 mesh, elution gradient: 30% ethyl acetate/hexanes to 40% ethyl acetate/hexanes) afforded 3-(iodomethyl)-1,1-dimethoxycyclobutane (1.34 g, 74% yield) as a light yellow oil.1H NMR (300 MHz, CDCl3) δ ppm: 1.72- 1.81 (m, 2H, CH2), 2.28-2.53 (m, 3H, CH2 and CH), 3.14 (s, 3H, OCH3), 3.16 (s, 3H, OCH3), 3.29 (d, J = 7.7 Hz, 2H, ICH2).

References

[1] Patent: US2008/21032, 2008, A1. Location in patent: Page/Page column 83-84