Hydrochloric Acid → HCID 53642910, compound

Participants

Reaction Steps

2-Ethylthio-1-nitrobutene was prepared by adding a solution of sulfuryl chloride (20.16 g., 0.149 mol) in methylene chloride (30 ml.) to a stirred solution of 2-ethylthio-1-nitrobutane (23.02 g., 0.141 mol) in methylene chloride (100 ml.) at 0° C. The resulting solution was stirred for 15 minutes after addition was complete, and the volatile components were removed under reduced pressure. The residue was dissolved in methylene chloride (100 ml.) and a solution of triethylamine (14.27 g., 0.141 mol) in methylene chloride (30 ml.) was added at 0C. Once addition was complete, the solution was stirred for 15 minutes, and then was poured into dilute aqueous hydrochloric acid solution (400 ml.). The organics were separated and washed with deionized water (2×75 ml.), dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography(10:1 hexanes/ethyl acetate) yielded the product as a yellow oil, 2.85 g., 13% yield. 1H-NMR (CDCl3): δ 1.26, m, 3H, --CH3 ; 1.36, m, 3H, --CH3 ; 2.55, q, 2H, --CH2 --; 2.92, q, 2H, SCH2 --; 7.2, s, 1H, olefinic H.

Provenance & Evidence