Isoamyl Nitrite → HCID 18668838, compound

Participants

Reaction Steps

A solution of methylsulfide 5 (37 mg, 0.1 mmol) in DMF (5 mL) was warmed up to 65° C. and treated dropwise with excess isoamyl nitrite. After a few minutes nitrogen gas bubbled off the reaction mixture. The stirring was continued for 30 min. The reaction was cooled down to room temperature, diluted with ethyl ether (10 mL) and washed with brine (5×15 mL). The organic layer was dried (magnesium sulfate) and the solvents removed at reduced pressure, leaving a dark oil residue The desired product was obtained upon flash chromatography eluting with ethyl acetate-hexanes (5%), to yield 19 mg (54%) of desired product 8. 1H-NMR (δ, CDCl3): 7.95 (1H, s); 7.78 (2H, s); 2.6 (3H; s). MS: M+1=352 (calculated: 352).

Provenance & Evidence