Hydrochloric Acid → 2-[(3-Chloro-3-methyl-2-nitrosobutoxy)methyl]-5-nitrofuran

Participants

Reaction Conditions

Reaction Steps

Concentrated HCl (2.5 mL) was added to a cooled (0°-5° C.) solution of isoamyl nitrite (14.0 g, 0.12 mol) and 2-[[(3-methyl-2-butenyl)oxy]methyl]-5-nitrofuran (4.0 g, 0.06 mol). The temperature was maintained below 5° C. during the addition and the reaction mixture was stirred at 5° C. for an additional 30 min. The product was filtered and washed with a cold (-20° C.) 1:1 mixture of ethanol and ether. The solid was further washed with ether to afford a light yellow solid. Yield 2.6 g (52%). mp 134°-135° C. 1H NMR (DMSO) 1.78 (ε 6H, CH3), 4.44 (s, 2H, HON=CCH2), 4.67 (s, 2H, CH2OAr ), 6.6 and 7.27 (d, 2H, ArH). MS: 277 (M+H)+

Provenance & Evidence